diff --git a/components/ambient-ui/package-lock.json b/components/ambient-ui/package-lock.json
index ad76a4a17..ad07f874e 100644
--- a/components/ambient-ui/package-lock.json
+++ b/components/ambient-ui/package-lock.json
@@ -8,6 +8,7 @@
       "name": "ambient-ui",
       "version": "0.1.0",
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         "@radix-ui/react-tooltip": "^1.2.8",
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         "@tanstack/react-query": "^5.90.2",
         "@tanstack/react-table": "^8.21.3",
         "ambient-sdk": "file:../ambient-sdk/ts-sdk",
@@ -30,7 +32,9 @@
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         "react": "^19.1.0",
         "react-dom": "^19.1.0",
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+      "resolved": "https://registry.npmjs.org/@radix-ui/react-alert-dialog/-/react-alert-dialog-1.1.15.tgz",
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+      "license": "MIT",
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+      "resolved": "https://registry.npmjs.org/@radix-ui/react-primitive/-/react-primitive-2.1.3.tgz",
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+      "license": "MIT",
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@@ -3774,6 +3862,18 @@
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-      "dev": true,
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+      "license": "MIT",
+      "dependencies": {
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@@ -3967,6 +4093,21 @@
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@@ -3997,6 +4137,12 @@
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@@ -4292,6 +4438,12 @@
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+      "resolved": "https://registry.npmjs.org/@ungap/structured-clone/-/structured-clone-1.3.1.tgz",
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@@ -5076,6 +5228,16 @@
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+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/wooorm"
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+      "license": "MIT",
+      "funding": {
+        "type": "github",
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+      "funding": {
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@@ -5317,6 +5529,16 @@
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+      "funding": {
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+      "integrity": "sha512-xKvGhPWw3k84Qjh8bI3ZeJjqnyadK+GEFtazSfZv/rKeTkTjOJho6mFqh2SM96iIcZokxiOpg78GazTSg8+KHA==",
+      "license": "MIT",
+      "dependencies": {
+        "@types/unist": "^3.0.0",
+        "bail": "^2.0.0",
+        "devlop": "^1.0.0",
+        "extend": "^3.0.0",
+        "is-plain-obj": "^4.0.0",
+        "trough": "^2.0.0",
+        "vfile": "^6.0.0"
+      },
+      "funding": {
+        "type": "opencollective",
+        "url": "https://opencollective.com/unified"
+      }
+    },
+    "node_modules/unist-util-is": {
+      "version": "6.0.1",
+      "resolved": "https://registry.npmjs.org/unist-util-is/-/unist-util-is-6.0.1.tgz",
+      "integrity": "sha512-LsiILbtBETkDz8I9p1dQ0uyRUWuaQzd/cuEeS1hoRSyW5E5XGmTzlwY1OrNzzakGowI9Dr/I8HVaw4hTtnxy8g==",
+      "license": "MIT",
+      "dependencies": {
+        "@types/unist": "^3.0.0"
+      },
+      "funding": {
+        "type": "opencollective",
+        "url": "https://opencollective.com/unified"
+      }
+    },
+    "node_modules/unist-util-position": {
+      "version": "5.0.0",
+      "resolved": "https://registry.npmjs.org/unist-util-position/-/unist-util-position-5.0.0.tgz",
+      "integrity": "sha512-fucsC7HjXvkB5R3kTCO7kUjRdrS0BJt3M/FPxmHMBOm8JQi2BsHAHFsy27E0EolP8rp0NzXsJ+jNPyDWvOJZPA==",
+      "license": "MIT",
+      "dependencies": {
+        "@types/unist": "^3.0.0"
+      },
+      "funding": {
+        "type": "opencollective",
+        "url": "https://opencollective.com/unified"
+      }
+    },
+    "node_modules/unist-util-stringify-position": {
+      "version": "4.0.0",
+      "resolved": "https://registry.npmjs.org/unist-util-stringify-position/-/unist-util-stringify-position-4.0.0.tgz",
+      "integrity": "sha512-0ASV06AAoKCDkS2+xw5RXJywruurpbC4JZSm7nr7MOt1ojAzvyyaO+UxZf18j8FCF6kmzCZKcAgN/yu2gm2XgQ==",
+      "license": "MIT",
+      "dependencies": {
+        "@types/unist": "^3.0.0"
+      },
+      "funding": {
+        "type": "opencollective",
+        "url": "https://opencollective.com/unified"
+      }
+    },
+    "node_modules/unist-util-visit": {
+      "version": "5.1.0",
+      "resolved": "https://registry.npmjs.org/unist-util-visit/-/unist-util-visit-5.1.0.tgz",
+      "integrity": "sha512-m+vIdyeCOpdr/QeQCu2EzxX/ohgS8KbnPDgFni4dQsfSCtpz8UqDyY5GjRru8PDKuYn7Fq19j1CQ+nJSsGKOzg==",
+      "license": "MIT",
+      "dependencies": {
+        "@types/unist": "^3.0.0",
+        "unist-util-is": "^6.0.0",
+        "unist-util-visit-parents": "^6.0.0"
+      },
+      "funding": {
+        "type": "opencollective",
+        "url": "https://opencollective.com/unified"
+      }
+    },
+    "node_modules/unist-util-visit-parents": {
+      "version": "6.0.2",
+      "resolved": "https://registry.npmjs.org/unist-util-visit-parents/-/unist-util-visit-parents-6.0.2.tgz",
+      "integrity": "sha512-goh1s1TBrqSqukSc8wrjwWhL0hiJxgA8m4kFxGlQ+8FYQ3C/m11FcTs4YYem7V664AhHVvgoQLk890Ssdsr2IQ==",
+      "license": "MIT",
+      "dependencies": {
+        "@types/unist": "^3.0.0",
+        "unist-util-is": "^6.0.0"
+      },
+      "funding": {
+        "type": "opencollective",
+        "url": "https://opencollective.com/unified"
+      }
+    },
     "node_modules/unrs-resolver": {
       "version": "1.12.2",
       "resolved": "https://registry.npmjs.org/unrs-resolver/-/unrs-resolver-1.12.2.tgz",
@@ -9997,6 +11535,40 @@
         "react": "^16.8.0 || ^17.0.0 || ^18.0.0 || ^19.0.0"
       }
     },
+    "node_modules/util-deprecate": {
+      "version": "1.0.2",
+      "resolved": "https://registry.npmjs.org/util-deprecate/-/util-deprecate-1.0.2.tgz",
+      "integrity": "sha512-EPD5q1uXyFxJpCrLnCc1nHnq3gOa6DZBocAIiI2TaSCA7VCJ1UJDMagCzIkXNsUYfD1daK//LTEQ8xiIbrHtcw==",
+      "license": "MIT"
+    },
+    "node_modules/vfile": {
+      "version": "6.0.3",
+      "resolved": "https://registry.npmjs.org/vfile/-/vfile-6.0.3.tgz",
+      "integrity": "sha512-KzIbH/9tXat2u30jf+smMwFCsno4wHVdNmzFyL+T/L3UGqqk6JKfVqOFOZEpZSHADH1k40ab6NUIXZq422ov3Q==",
+      "license": "MIT",
+      "dependencies": {
+        "@types/unist": "^3.0.0",
+        "vfile-message": "^4.0.0"
+      },
+      "funding": {
+        "type": "opencollective",
+        "url": "https://opencollective.com/unified"
+      }
+    },
+    "node_modules/vfile-message": {
+      "version": "4.0.3",
+      "resolved": "https://registry.npmjs.org/vfile-message/-/vfile-message-4.0.3.tgz",
+      "integrity": "sha512-QTHzsGd1EhbZs4AsQ20JX1rC3cOlt/IWJruk893DfLRr57lcnOeMaWG4K0JrRta4mIJZKth2Au3mM3u03/JWKw==",
+      "license": "MIT",
+      "dependencies": {
+        "@types/unist": "^3.0.0",
+        "unist-util-stringify-position": "^4.0.0"
+      },
+      "funding": {
+        "type": "opencollective",
+        "url": "https://opencollective.com/unified"
+      }
+    },
     "node_modules/vite": {
       "version": "8.0.16",
       "resolved": "https://registry.npmjs.org/vite/-/vite-8.0.16.tgz",
@@ -10416,6 +11988,16 @@
       "funding": {
         "url": "https://github.com/sponsors/colinhacks"
       }
+    },
+    "node_modules/zwitch": {
+      "version": "2.0.4",
+      "resolved": "https://registry.npmjs.org/zwitch/-/zwitch-2.0.4.tgz",
+      "integrity": "sha512-bXE4cR/kVZhKZX/RjPEflHaKVhUVl85noU3v6b8apfQEc1x4A+zBxjZ4lN8LqGd6WZ3dl98pY4o717VFmoPp+A==",
+      "license": "MIT",
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/wooorm"
+      }
     }
   }
 }
diff --git a/components/ambient-ui/package.json b/components/ambient-ui/package.json
index 1415e2c2b..49b663b7d 100644
--- a/components/ambient-ui/package.json
+++ b/components/ambient-ui/package.json
@@ -13,6 +13,7 @@
     "test:e2e": "npx playwright test"
   },
   "dependencies": {
+    "@radix-ui/react-alert-dialog": "^1.1.15",
     "@radix-ui/react-avatar": "^1.1.10",
     "@radix-ui/react-dialog": "^1.1.15",
     "@radix-ui/react-dropdown-menu": "^2.1.16",
@@ -22,6 +23,7 @@
     "@radix-ui/react-slot": "^1.2.4",
     "@radix-ui/react-tabs": "^1.1.13",
     "@radix-ui/react-tooltip": "^1.2.8",
+    "@tailwindcss/typography": "^0.5.19",
     "@tanstack/react-query": "^5.90.2",
     "@tanstack/react-table": "^8.21.3",
     "ambient-sdk": "file:../ambient-sdk/ts-sdk",
@@ -35,7 +37,9 @@
     "openid-client": "^6.8.4",
     "react": "^19.1.0",
     "react-dom": "^19.1.0",
+    "react-markdown": "^10.1.0",
     "react-resizable-panels": "^3.0.6",
+    "remark-gfm": "^4.0.1",
     "sonner": "^2.0.7",
     "tailwind-merge": "^3.3.1",
     "tw-animate-css": "^1.4.0",
diff --git a/components/ambient-ui/src/adapters/sdk-sessions.ts b/components/ambient-ui/src/adapters/sdk-sessions.ts
index a5c141738..d2f7d7e88 100644
--- a/components/ambient-ui/src/adapters/sdk-sessions.ts
+++ b/components/ambient-ui/src/adapters/sdk-sessions.ts
@@ -51,6 +51,10 @@ function createSdkSessionsAdapter(api: SessionAPI): SessionsPort {
       const session = await api.start(sessionId)
       return mapSdkSessionToDomain(session)
     },
+
+    async delete(sessionId: string): Promise<void> {
+      await api.delete(sessionId)
+    },
   }
 }
 
diff --git a/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/[sessionId]/_components/chat-tab.tsx b/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/[sessionId]/_components/chat-tab.tsx
new file mode 100644
index 000000000..1129d3c1a
--- /dev/null
+++ b/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/[sessionId]/_components/chat-tab.tsx
@@ -0,0 +1,186 @@
+'use client'
+
+import { useMemo, useRef, useEffect, useState, useCallback } from 'react'
+import { ExternalLink, ArrowDownLeft, Bot, ChevronUp, ChevronDown } from 'lucide-react'
+import { Button } from '@/components/ui/button'
+import { Card, CardContent } from '@/components/ui/card'
+import { Tooltip, TooltipContent, TooltipProvider, TooltipTrigger } from '@/components/ui/tooltip'
+import type { DomainSession } from '@/domain/types'
+import { useSessionMessages } from '@/queries/use-session-messages'
+import {
+  ChatItemsList,
+  ChatInput,
+  buildChatItems,
+} from '@/components/chat-messages'
+import { useChatSidebar } from '@/components/chat-sidebar-context'
+import { useLiveTail, LiveIndicator } from './live-tail-indicator'
+
+// ---- Main Chat Tab ----
+
+export function ChatTab({ session }: { session: DomainSession }) {
+  const { data, isLoading, error } = useSessionMessages(session.id)
+  const { openSessionId, openSidebar, closeSidebar } = useChatSidebar()
+  const isInSidebar = openSessionId === session.id
+
+  const chatItems = useMemo(() => {
+    return buildChatItems(data?.items ?? [])
+  }, [data])
+
+  const chatItemCount = chatItems.length
+
+  const [showScrollToTop, setShowScrollToTop] = useState(false)
+  const [scrolledUp, setScrolledUp] = useState(false)
+
+  const { scrollRef, sentinelRef, isAtBottom, newEventCount, scrollToBottom } =
+    useLiveTail(chatItemCount)
+
+  const handleScroll = useCallback(() => {
+    const container = scrollRef.current
+    if (!container) return
+    setShowScrollToTop(container.scrollTop > 300)
+    const atBottom = container.scrollHeight - container.scrollTop - container.clientHeight < 50
+    setScrolledUp(!atBottom)
+  }, [scrollRef])
+
+  const scrollToTop = useCallback(() => {
+    scrollRef.current?.scrollTo({ top: 0, behavior: 'smooth' })
+  }, [scrollRef])
+
+  // Auto-scroll on initial load
+  const hasScrolledOnLoad = useRef(false)
+  useEffect(() => {
+    if (!isLoading && chatItemCount > 0 && !hasScrolledOnLoad.current) {
+      hasScrolledOnLoad.current = true
+      requestAnimationFrame(() => {
+        scrollToBottom()
+      })
+    }
+  }, [isLoading, chatItemCount, scrollToBottom])
+
+  if (error) {
+    return (
+      <div className="pt-4">
+        <p className="text-sm text-destructive">
+          Failed to load messages: {error.message}
+        </p>
+      </div>
+    )
+  }
+
+  // When the chat is open in the sidebar, show a placeholder with bring-back option
+  if (isInSidebar) {
+    return (
+      <div className="pt-4">
+        <Card className="flex flex-col items-center justify-center py-16 p-0">
+          <CardContent className="flex flex-col items-center gap-4 text-center p-6">
+            <Bot className="h-10 w-10 text-muted-foreground opacity-40" aria-hidden="true" />
+            <div>
+              <p className="text-sm font-medium text-foreground">
+                Chat is open in the sidebar
+              </p>
+              <p className="text-xs text-muted-foreground mt-1">
+                You can continue chatting from the sidebar while navigating other pages.
+              </p>
+            </div>
+            <Button
+              variant="outline"
+              size="sm"
+              onClick={() => closeSidebar()}
+              aria-label="Bring chat back to this tab"
+            >
+              <ArrowDownLeft className="h-4 w-4 mr-1.5" />
+              Bring back
+            </Button>
+          </CardContent>
+        </Card>
+      </div>
+    )
+  }
+
+  return (
+    <div className="pt-4">
+      <Card className="flex flex-col overflow-hidden p-0">
+        {/* Header with pop-out button */}
+        <div className="flex items-center justify-between border-b px-4 py-2">
+          <div className="flex items-center gap-2">
+            {isAtBottom && chatItemCount > 0 && <LiveIndicator />}
+          </div>
+          <Button
+            variant="ghost"
+            size="sm"
+            onClick={() => openSidebar(session.id)}
+            aria-label="Pop out chat to sidebar"
+            className="text-xs text-muted-foreground hover:text-foreground"
+          >
+            <ExternalLink className="h-3.5 w-3.5 mr-1.5" />
+            Pop out
+          </Button>
+        </div>
+
+        {/* Message area */}
+        <CardContent className="flex-1 p-0 relative">
+          <div
+            ref={scrollRef}
+            className="max-h-[600px] overflow-y-auto"
+            role="log"
+            aria-label="Chat messages"
+            onScroll={handleScroll}
+          >
+            <ChatItemsList items={chatItems} isLoading={isLoading} />
+            <div ref={sentinelRef} className="h-1" aria-hidden="true" />
+          </div>
+
+          {/* Scroll buttons */}
+          <TooltipProvider>
+            <div className="absolute bottom-3 right-3 z-10 flex flex-col gap-1">
+              <div className={`transition-all duration-200 ${showScrollToTop ? 'opacity-100 scale-100' : 'opacity-0 scale-75 pointer-events-none'}`}>
+                <Tooltip>
+                  <TooltipTrigger asChild>
+                    <Button
+                      variant="outline"
+                      size="icon"
+                      className="h-7 w-7 rounded-full shadow-md cursor-pointer"
+                      onClick={scrollToTop}
+                      aria-label="Scroll to top"
+                    >
+                      <ChevronUp className="h-4 w-4" />
+                    </Button>
+                  </TooltipTrigger>
+                  <TooltipContent side="left">Scroll to top</TooltipContent>
+                </Tooltip>
+              </div>
+              <div className={`transition-all duration-200 ${scrolledUp && chatItemCount > 0 ? 'opacity-100 scale-100' : 'opacity-0 scale-75 pointer-events-none'}`}>
+                <Tooltip>
+                  <TooltipTrigger asChild>
+                    <Button
+                      variant="outline"
+                      size="icon"
+                      className="h-7 w-7 rounded-full shadow-md cursor-pointer"
+                      onClick={scrollToBottom}
+                      aria-label="Scroll to bottom"
+                    >
+                      <ChevronDown className="h-4 w-4" />
+                      {newEventCount > 0 && (
+                        <span className="absolute -top-1 -right-1 flex h-4 min-w-4 items-center justify-center rounded-full bg-primary text-[10px] font-bold text-primary-foreground px-1">
+                          {newEventCount}
+                        </span>
+                      )}
+                    </Button>
+                  </TooltipTrigger>
+                  <TooltipContent side="left">Scroll to bottom</TooltipContent>
+                </Tooltip>
+              </div>
+            </div>
+          </TooltipProvider>
+        </CardContent>
+
+        {/* Input area */}
+        <ChatInput
+          sessionId={session.id}
+          phase={session.phase}
+          disabled={isLoading}
+        />
+      </Card>
+    </div>
+  )
+}
diff --git a/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/[sessionId]/_components/session-header.tsx b/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/[sessionId]/_components/session-header.tsx
index f410a4def..86f8d2e1e 100644
--- a/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/[sessionId]/_components/session-header.tsx
+++ b/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/[sessionId]/_components/session-header.tsx
@@ -1,96 +1,238 @@
 'use client'
 
-import { useState } from 'react'
-import { ExternalLink, Square, RotateCcw } from 'lucide-react'
+import { useState, useCallback } from 'react'
+import { useRouter, useParams } from 'next/navigation'
+import { ExternalLink, Square, RotateCcw, Download, Trash2, MoreVertical } from 'lucide-react'
 import type { DomainSession } from '@/domain/types'
 import { getPreviewAnnotations } from '@/domain/annotations'
-import { useStopSession, useStartSession } from '@/queries/use-sessions'
+import { useStopSession, useStartSession, useDeleteSession } from '@/queries/use-sessions'
 import { useSendFeedback } from '@/queries/use-send-feedback'
 import { PhaseBadge } from '../../_components/phase-badge'
 import { formatDuration, formatRelativeTime } from '@/lib/format-timestamp'
 import { Button } from '@/components/ui/button'
 import { PreviewOverlay } from '@/components/preview/preview-overlay'
+import {
+  DropdownMenu,
+  DropdownMenuContent,
+  DropdownMenuItem,
+  DropdownMenuSeparator,
+  DropdownMenuTrigger,
+} from '@/components/ui/dropdown-menu'
+import {
+  AlertDialog,
+  AlertDialogAction,
+  AlertDialogCancel,
+  AlertDialogContent,
+  AlertDialogDescription,
+  AlertDialogFooter,
+  AlertDialogHeader,
+  AlertDialogTitle,
+} from '@/components/ui/alert-dialog'
 
 const STOPPABLE_PHASES = new Set(['Running', 'Pending', 'Creating'])
 const RESTARTABLE_PHASES = new Set(['Completed', 'Failed', 'Stopped'])
 
 export function SessionHeader({ session }: { session: DomainSession }) {
   const [previewOpen, setPreviewOpen] = useState(false)
+  const [stopDialogOpen, setStopDialogOpen] = useState(false)
+  const [deleteDialogOpen, setDeleteDialogOpen] = useState(false)
+
+  const router = useRouter()
+  const { projectId } = useParams<{ projectId: string; sessionId: string }>()
+
   const stopSession = useStopSession()
   const startSession = useStartSession()
+  const deleteSession = useDeleteSession()
   const sendFeedback = useSendFeedback()
 
   const preview = getPreviewAnnotations(session.annotations)
   const canStop = STOPPABLE_PHASES.has(session.phase)
   const canRestart = RESTARTABLE_PHASES.has(session.phase)
 
+  const handleConfirmStop = useCallback(() => {
+    stopSession.mutate(session.id, {
+      onSettled: () => setStopDialogOpen(false),
+    })
+  }, [stopSession, session.id])
+
+  const handleConfirmDelete = useCallback(() => {
+    deleteSession.mutate(session.id, {
+      onSuccess: () => {
+        setDeleteDialogOpen(false)
+        router.push(`/${projectId}/fleet`)
+      },
+      onError: () => setDeleteDialogOpen(false),
+    })
+  }, [deleteSession, session.id, router, projectId])
+
+  const handleExport = useCallback(async () => {
+    const { createSessionMessagesAdapterWithFetch } = await import('@/adapters/session-messages')
+    const adapter = createSessionMessagesAdapterWithFetch()
+    const result = await adapter.list(session.id, { size: 1000 })
+
+    const exportData = {
+      session: {
+        id: session.id,
+        name: session.name,
+        phase: session.phase,
+        agentName: session.agentName,
+        model: session.model,
+        createdAt: session.createdAt,
+        startTime: session.startTime,
+        completionTime: session.completionTime,
+      },
+      messages: result.items,
+      exportedAt: new Date().toISOString(),
+    }
+
+    const blob = new Blob([JSON.stringify(exportData, null, 2)], {
+      type: 'application/json',
+    })
+    const url = URL.createObjectURL(blob)
+    const link = document.createElement('a')
+    link.href = url
+    link.download = `session-${session.name || session.id}.json`
+    document.body.appendChild(link)
+    link.click()
+    document.body.removeChild(link)
+    URL.revokeObjectURL(url)
+  }, [session])
+
   return (
     <>
-      <div className="space-y-3">
-        <div className="flex items-center justify-between">
-          <div className="flex items-center gap-3">
-            <h1 className="text-2xl font-semibold">{session.name}</h1>
-            <PhaseBadge phase={session.phase} />
+      <div className="sticky top-0 z-[5] bg-background/95 backdrop-blur supports-[backdrop-filter]:bg-background/60 pb-4 -mx-1 px-1">
+        <div className="space-y-3">
+          <div className="flex items-center justify-between">
+            <div className="flex items-center gap-3">
+              <h1 className="text-2xl font-semibold">{session.name}</h1>
+              <PhaseBadge phase={session.phase} />
+            </div>
+
+            <div className="flex items-center gap-2">
+              {preview && (
+                <Button
+                  variant="outline"
+                  size="sm"
+                  onClick={() => setPreviewOpen(true)}
+                  aria-label="Open preview"
+                >
+                  <ExternalLink className="h-4 w-4" />
+                  Preview
+                </Button>
+              )}
+
+              {canStop && (
+                <Button
+                  variant="destructive"
+                  size="sm"
+                  onClick={() => setStopDialogOpen(true)}
+                  disabled={stopSession.isPending}
+                  aria-label="Stop session"
+                >
+                  <Square className="h-4 w-4" />
+                  Stop
+                </Button>
+              )}
+
+              {canRestart && (
+                <Button
+                  variant="outline"
+                  size="sm"
+                  onClick={() => startSession.mutate(session.id)}
+                  disabled={startSession.isPending}
+                  aria-label="Restart session"
+                >
+                  <RotateCcw className="h-4 w-4" />
+                  Restart
+                </Button>
+              )}
+
+              <DropdownMenu>
+                <DropdownMenuTrigger asChild>
+                  <Button variant="ghost" size="icon" className="h-8 w-8" aria-label="More actions">
+                    <MoreVertical className="h-4 w-4" />
+                  </Button>
+                </DropdownMenuTrigger>
+                <DropdownMenuContent align="end">
+                  <DropdownMenuItem onClick={handleExport}>
+                    <Download className="h-4 w-4 mr-2" />
+                    Export
+                  </DropdownMenuItem>
+                  <DropdownMenuSeparator />
+                  <DropdownMenuItem
+                    onClick={() => setDeleteDialogOpen(true)}
+                    disabled={deleteSession.isPending}
+                    className="text-destructive focus:text-destructive"
+                  >
+                    <Trash2 className="h-4 w-4 mr-2" />
+                    Delete
+                  </DropdownMenuItem>
+                </DropdownMenuContent>
+              </DropdownMenu>
+            </div>
           </div>
 
-          <div className="flex items-center gap-2">
-            {preview && (
-              <Button
-                variant="outline"
-                size="sm"
-                onClick={() => setPreviewOpen(true)}
-                aria-label="Open preview"
-              >
-                <ExternalLink />
-                Open Preview
-              </Button>
+          <div className="flex items-center gap-6 text-sm text-muted-foreground">
+            {session.agentName && (
+              <MetaItem label="Agent" value={session.agentName} />
             )}
-
-            {canStop && (
-              <Button
-                variant="destructive"
-                size="sm"
-                onClick={() => stopSession.mutate(session.id)}
-                disabled={stopSession.isPending}
-                aria-label="Stop session"
-              >
-                <Square />
-                Stop
-              </Button>
+            {session.model && (
+              <MetaItem label="Model" value={session.model} />
             )}
-
-            {canRestart && (
-              <Button
-                variant="outline"
-                size="sm"
-                onClick={() => startSession.mutate(session.id)}
-                disabled={startSession.isPending}
-                aria-label="Restart session"
-              >
-                <RotateCcw />
-                Restart
-              </Button>
+            {session.startTime && (
+              <MetaItem
+                label="Duration"
+                value={formatDuration(session.startTime, session.completionTime)}
+              />
             )}
+            <MetaItem label="Created" value={formatRelativeTime(session.createdAt)} />
           </div>
         </div>
-
-        <div className="flex items-center gap-6 text-sm text-muted-foreground">
-          {session.agentName && (
-            <MetaItem label="Agent" value={session.agentName} />
-          )}
-          {session.model && (
-            <MetaItem label="Model" value={session.model} />
-          )}
-          {session.startTime && (
-            <MetaItem
-              label="Duration"
-              value={formatDuration(session.startTime, session.completionTime)}
-            />
-          )}
-          <MetaItem label="Created" value={formatRelativeTime(session.createdAt)} />
-        </div>
       </div>
 
+      {/* Stop confirmation dialog */}
+      <AlertDialog open={stopDialogOpen} onOpenChange={setStopDialogOpen}>
+        <AlertDialogContent>
+          <AlertDialogHeader>
+            <AlertDialogTitle>Stop this session?</AlertDialogTitle>
+            <AlertDialogDescription>
+              The agent will be terminated. Any in-progress work will be lost.
+            </AlertDialogDescription>
+          </AlertDialogHeader>
+          <AlertDialogFooter>
+            <AlertDialogCancel>Cancel</AlertDialogCancel>
+            <AlertDialogAction
+              onClick={handleConfirmStop}
+              className="bg-destructive text-white hover:bg-destructive/90"
+            >
+              Stop session
+            </AlertDialogAction>
+          </AlertDialogFooter>
+        </AlertDialogContent>
+      </AlertDialog>
+
+      {/* Delete confirmation dialog */}
+      <AlertDialog open={deleteDialogOpen} onOpenChange={setDeleteDialogOpen}>
+        <AlertDialogContent>
+          <AlertDialogHeader>
+            <AlertDialogTitle>Delete this session?</AlertDialogTitle>
+            <AlertDialogDescription>
+              This action cannot be undone. The session and all its data will be
+              permanently deleted.
+            </AlertDialogDescription>
+          </AlertDialogHeader>
+          <AlertDialogFooter>
+            <AlertDialogCancel>Cancel</AlertDialogCancel>
+            <AlertDialogAction
+              onClick={handleConfirmDelete}
+              className="bg-destructive text-white hover:bg-destructive/90"
+            >
+              Delete session
+            </AlertDialogAction>
+          </AlertDialogFooter>
+        </AlertDialogContent>
+      </AlertDialog>
+
       {previewOpen && preview && (
         <PreviewOverlay
           url={preview.url}
diff --git a/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/[sessionId]/page.tsx b/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/[sessionId]/page.tsx
index fa5548498..1d85f3ee9 100644
--- a/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/[sessionId]/page.tsx
+++ b/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/[sessionId]/page.tsx
@@ -1,5 +1,6 @@
 'use client'
 
+import { useState } from 'react'
 import { useParams } from 'next/navigation'
 import { Skeleton } from '@/components/ui/skeleton'
 import { Tabs, TabsContent, TabsList, TabsTrigger } from '@/components/ui/tabs'
@@ -7,11 +8,23 @@ import { useSession } from '@/queries/use-sessions'
 import { SessionHeader } from './_components/session-header'
 import { PhaseTab } from './_components/phase-tab'
 import { LogsTab } from './_components/logs-tab'
+import { ChatTab } from './_components/chat-tab'
 
 export default function SessionDetailPage() {
   const { sessionId } = useParams<{ projectId: string; sessionId: string }>()
+  const [activeTab, setActiveTab] = useState(() => {
+    if (typeof window === 'undefined') return 'phase'
+    return new URL(window.location.href).searchParams.get('tab') ?? 'phase'
+  })
   const { data: session, isLoading, error } = useSession(sessionId)
 
+  const handleTabChange = (value: string) => {
+    setActiveTab(value)
+    const url = new URL(window.location.href)
+    url.searchParams.set('tab', value)
+    window.history.replaceState({}, '', url.toString())
+  }
+
   if (error) {
     return (
       <p className="text-sm text-destructive">
@@ -32,13 +45,13 @@ export default function SessionDetailPage() {
   return (
     <div className="space-y-6">
       <SessionHeader session={session} />
-      <Tabs defaultValue="phase">
+      <Tabs value={activeTab} onValueChange={handleTabChange}>
         <TabsList className="w-full *:flex-1">
           <TabsTrigger value="phase">Phase</TabsTrigger>
           <TabsTrigger value="logs">Logs</TabsTrigger>
           <TabsTrigger value="resources" disabled>Resources</TabsTrigger>
           <TabsTrigger value="details" disabled>Details</TabsTrigger>
-          <TabsTrigger value="chat" disabled>Chat</TabsTrigger>
+          <TabsTrigger value="chat">Chat</TabsTrigger>
         </TabsList>
         <TabsContent value="phase">
           <PhaseTab session={session} />
@@ -46,6 +59,9 @@ export default function SessionDetailPage() {
         <TabsContent value="logs">
           <LogsTab session={session} />
         </TabsContent>
+        <TabsContent value="chat">
+          <ChatTab session={session} />
+        </TabsContent>
       </Tabs>
     </div>
   )
diff --git a/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/_components/fleet-columns.tsx b/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/_components/fleet-columns.tsx
index cb6bba301..1107be31f 100644
--- a/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/_components/fleet-columns.tsx
+++ b/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/_components/fleet-columns.tsx
@@ -1,11 +1,48 @@
 import { createColumnHelper } from '@tanstack/react-table'
+import { MessageSquare } from 'lucide-react'
+import { Button } from '@/components/ui/button'
+import {
+  Tooltip,
+  TooltipContent,
+  TooltipTrigger,
+} from '@/components/ui/tooltip'
 import type { DomainSession } from '@/domain/types'
 import { formatRelativeTime, formatDuration } from '@/lib/format-timestamp'
+import { useChatSidebar } from '@/components/chat-sidebar-context'
 import { PhaseBadge } from './phase-badge'
 
 const COST_ANNOTATION = 'ambient-code.io/cost/estimate'
 const col = createColumnHelper<DomainSession>()
 
+function ChatColumnButton({ sessionId }: { sessionId: string }) {
+  const { openSidebar, openSessionId } = useChatSidebar()
+  const isActive = openSessionId === sessionId
+
+  return (
+    <Tooltip>
+      <TooltipTrigger asChild>
+        <Button
+          variant="ghost"
+          size="icon"
+          className="h-7 w-7"
+          onClick={(e) => {
+            e.stopPropagation()
+            openSidebar(sessionId)
+          }}
+          aria-label="Open chat sidebar"
+        >
+          <MessageSquare
+            className={`h-4 w-4 ${isActive ? 'text-primary' : 'text-muted-foreground'}`}
+          />
+        </Button>
+      </TooltipTrigger>
+      <TooltipContent>
+        {isActive ? 'Chat sidebar is open' : 'Open chat in sidebar'}
+      </TooltipContent>
+    </Tooltip>
+  )
+}
+
 export const fleetColumns = [
   col.accessor('phase', {
     header: 'Phase',
@@ -72,4 +109,10 @@ export const fleetColumns = [
     },
     size: 80,
   }),
+  col.display({
+    id: 'chat',
+    header: '',
+    cell: ({ row }) => <ChatColumnButton sessionId={row.original.id} />,
+    size: 48,
+  }),
 ]
diff --git a/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/_components/fleet-table.tsx b/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/_components/fleet-table.tsx
index 3f12b4115..c54843d2b 100644
--- a/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/_components/fleet-table.tsx
+++ b/components/ambient-ui/src/app/(dashboard)/[projectId]/fleet/_components/fleet-table.tsx
@@ -15,6 +15,7 @@ import {
   TableHeader,
   TableRow,
 } from '@/components/ui/table'
+import { TooltipProvider } from '@/components/ui/tooltip'
 import type { DomainSession } from '@/domain/types'
 import { fleetColumns } from './fleet-columns'
 
@@ -38,6 +39,7 @@ export function FleetTable({
   })
 
   return (
+    <TooltipProvider>
     <div className="rounded-md border">
       <Table>
         <TableHeader>
@@ -78,5 +80,6 @@ export function FleetTable({
         </TableBody>
       </Table>
     </div>
+    </TooltipProvider>
   )
 }
diff --git a/components/ambient-ui/src/app/(dashboard)/layout.tsx b/components/ambient-ui/src/app/(dashboard)/layout.tsx
index f2159985e..c5dc176b9 100644
--- a/components/ambient-ui/src/app/(dashboard)/layout.tsx
+++ b/components/ambient-ui/src/app/(dashboard)/layout.tsx
@@ -4,6 +4,8 @@ import { usePathname } from 'next/navigation'
 import { AppSidebar } from '@/components/app-sidebar'
 import { NavHeader } from '@/components/nav-header'
 import { StatusBar } from '@/components/status-bar'
+import { ChatSidebar } from '@/components/chat-sidebar'
+import { ChatSidebarProvider } from '@/components/chat-sidebar-context'
 import { useProject } from '@/queries/use-projects'
 import {
   SidebarInset,
@@ -31,17 +33,20 @@ export default function DashboardLayout({
   const { data: project } = useProject(projectId ?? '')
 
   return (
-    <SidebarProvider>
-      <AppSidebar projectId={projectId} />
-      <SidebarInset>
-        <NavHeader
-          projectId={projectId}
-          projectName={project?.name ?? null}
-          pageName={pageName}
-        />
-        <div className="flex-1 p-6 pb-10">{children}</div>
-        <StatusBar />
-      </SidebarInset>
-    </SidebarProvider>
+    <ChatSidebarProvider>
+      <SidebarProvider>
+        <AppSidebar projectId={projectId} />
+        <SidebarInset className="min-w-0 flex-1 overflow-x-clip">
+          <NavHeader
+            projectId={projectId}
+            projectName={project?.name ?? null}
+            pageName={pageName}
+          />
+          <div className="flex-1 p-6 pb-10">{children}</div>
+          <StatusBar />
+        </SidebarInset>
+        <ChatSidebar />
+      </SidebarProvider>
+    </ChatSidebarProvider>
   )
 }
diff --git a/components/ambient-ui/src/app/globals.css b/components/ambient-ui/src/app/globals.css
index 77390a300..cd17cca0e 100644
--- a/components/ambient-ui/src/app/globals.css
+++ b/components/ambient-ui/src/app/globals.css
@@ -1,5 +1,6 @@
 @import "tailwindcss";
 @import "tw-animate-css";
+@plugin "@tailwindcss/typography";
 
 @custom-variant dark (&:is(.dark *));
 
diff --git a/components/ambient-ui/src/components/__tests__/chat-messages.test.ts b/components/ambient-ui/src/components/__tests__/chat-messages.test.ts
new file mode 100644
index 000000000..3a516a3ba
--- /dev/null
+++ b/components/ambient-ui/src/components/__tests__/chat-messages.test.ts
@@ -0,0 +1,458 @@
+import { describe, it, expect } from 'vitest'
+import type { DomainSessionMessage } from '@/domain/types'
+import {
+  tryParseToolPayload,
+  tryParseToolResult,
+  extractLastAssistantMessage,
+  enrichMessages,
+  groupChatItems,
+  buildChatItems,
+} from '../chat-messages'
+
+// ---- Factory ----
+
+let _seq = 0
+function makeMsg(
+  overrides: Partial<DomainSessionMessage> & Pick<DomainSessionMessage, 'eventType'>,
+): DomainSessionMessage {
+  _seq += 1
+  return {
+    id: `msg-${_seq}`,
+    sessionId: 'sess-1',
+    payload: '',
+    seq: _seq,
+    createdAt: new Date().toISOString(),
+    ...overrides,
+  }
+}
+
+// ---- tryParseToolPayload ----
+
+describe('tryParseToolPayload', () => {
+  it('extracts name from the "tool" field', () => {
+    const result = tryParseToolPayload(JSON.stringify({ tool: 'Read', tool_call_id: 'tc-1' }))
+    expect(result).not.toBeNull()
+    expect(result!.name).toBe('Read')
+  })
+
+  it('extracts name and arguments from "name" + "arguments" fields', () => {
+    const result = tryParseToolPayload(
+      JSON.stringify({ name: 'Bash', arguments: { command: 'ls' } }),
+    )
+    expect(result).not.toBeNull()
+    expect(result!.name).toBe('Bash')
+    expect(result!.arguments).toEqual({ command: 'ls' })
+  })
+
+  it('extracts arguments from the "input" field when "arguments" is absent', () => {
+    const result = tryParseToolPayload(
+      JSON.stringify({ tool: 'Write', input: { path: '/a' } }),
+    )
+    expect(result).not.toBeNull()
+    expect(result!.name).toBe('Write')
+    expect(result!.arguments).toEqual({ path: '/a' })
+  })
+
+  it('returns null for invalid JSON', () => {
+    expect(tryParseToolPayload('not json {')).toBeNull()
+  })
+
+  it('returns null for non-object JSON (array)', () => {
+    expect(tryParseToolPayload('[1,2,3]')).toBeNull()
+  })
+
+  it('returns null for non-object JSON (string)', () => {
+    expect(tryParseToolPayload('"hello"')).toBeNull()
+  })
+
+  it('returns null when neither "tool" nor "name" is present', () => {
+    expect(tryParseToolPayload(JSON.stringify({ arguments: {} }))).toBeNull()
+  })
+
+  it('returns empty arguments when neither "arguments" nor "input" is present', () => {
+    const result = tryParseToolPayload(JSON.stringify({ tool: 'Read' }))
+    expect(result).not.toBeNull()
+    expect(result!.arguments).toEqual({})
+  })
+})
+
+// ---- tryParseToolResult ----
+
+describe('tryParseToolResult', () => {
+  it('extracts result and toolCallId', () => {
+    const result = tryParseToolResult(
+      JSON.stringify({ tool_call_id: 'tc-1', result: 'output' }),
+    )
+    expect(result).not.toBeNull()
+    expect(result!.result).toBe('output')
+    expect(result!.toolCallId).toBe('tc-1')
+  })
+
+  it('strips wrapping double-quotes from result', () => {
+    const result = tryParseToolResult(
+      JSON.stringify({ tool_call_id: 'tc-2', result: '"wrapped value"' }),
+    )
+    expect(result).not.toBeNull()
+    expect(result!.result).toBe('wrapped value')
+  })
+
+  it('returns empty string toolCallId when tool_call_id is missing', () => {
+    const result = tryParseToolResult(JSON.stringify({ result: 'data' }))
+    expect(result).not.toBeNull()
+    expect(result!.toolCallId).toBe('')
+  })
+
+  it('returns null for invalid JSON', () => {
+    expect(tryParseToolResult('bad json')).toBeNull()
+  })
+
+  it('returns null for non-object JSON', () => {
+    expect(tryParseToolResult('42')).toBeNull()
+  })
+})
+
+// ---- extractLastAssistantMessage ----
+
+describe('extractLastAssistantMessage', () => {
+  it('extracts last_assistant_message from a system event payload', () => {
+    const payload = JSON.stringify({
+      value: { last_assistant_message: 'Hello from the assistant' },
+    })
+    expect(extractLastAssistantMessage(payload)).toBe('Hello from the assistant')
+  })
+
+  it('returns null when last_assistant_message is missing', () => {
+    const payload = JSON.stringify({ value: { other_field: 'x' } })
+    expect(extractLastAssistantMessage(payload)).toBeNull()
+  })
+
+  it('returns null when last_assistant_message is whitespace-only', () => {
+    const payload = JSON.stringify({ value: { last_assistant_message: '   ' } })
+    expect(extractLastAssistantMessage(payload)).toBeNull()
+  })
+
+  it('returns null when value is not an object', () => {
+    const payload = JSON.stringify({ value: 'string-value' })
+    expect(extractLastAssistantMessage(payload)).toBeNull()
+  })
+
+  it('returns null for invalid JSON', () => {
+    expect(extractLastAssistantMessage('not json')).toBeNull()
+  })
+
+  it('returns null for a JSON array', () => {
+    expect(extractLastAssistantMessage('[1]')).toBeNull()
+  })
+})
+
+// ---- enrichMessages ----
+
+describe('enrichMessages', () => {
+  it('enriches empty assistant messages from a preceding system event', () => {
+    const messages = [
+      makeMsg({
+        eventType: 'system',
+        payload: JSON.stringify({
+          value: { last_assistant_message: 'Extracted text' },
+        }),
+      }),
+      makeMsg({ eventType: 'assistant', payload: '' }),
+    ]
+
+    const result = enrichMessages(messages)
+    expect(result).toHaveLength(2)
+    // The system event passes through
+    expect(result[0].eventType).toBe('system')
+    // The assistant message is enriched
+    expect(result[1].eventType).toBe('assistant')
+    expect(result[1].payload).toBe('Extracted text')
+  })
+
+  it('drops empty assistant messages with no nearby system event', () => {
+    const messages = [
+      makeMsg({ eventType: 'user', payload: 'hello' }),
+      makeMsg({ eventType: 'assistant', payload: '' }),
+    ]
+
+    const result = enrichMessages(messages)
+    expect(result).toHaveLength(1)
+    expect(result[0].eventType).toBe('user')
+  })
+
+  it('drops empty assistant messages when system event lacks last_assistant_message', () => {
+    const messages = [
+      makeMsg({
+        eventType: 'system',
+        payload: JSON.stringify({ value: { some_other: 'data' } }),
+      }),
+      makeMsg({ eventType: 'assistant', payload: '' }),
+    ]
+
+    const result = enrichMessages(messages)
+    // System passes through, empty assistant is dropped
+    expect(result).toHaveLength(1)
+    expect(result[0].eventType).toBe('system')
+  })
+
+  it('passes through non-empty assistant messages unchanged', () => {
+    const messages = [
+      makeMsg({ eventType: 'assistant', payload: 'I have content' }),
+    ]
+
+    const result = enrichMessages(messages)
+    expect(result).toHaveLength(1)
+    expect(result[0].payload).toBe('I have content')
+  })
+
+  it('passes through non-assistant messages unchanged', () => {
+    const messages = [
+      makeMsg({ eventType: 'user', payload: 'question' }),
+      makeMsg({ eventType: 'tool_use', payload: '{}' }),
+      makeMsg({ eventType: 'lifecycle', payload: 'started' }),
+    ]
+
+    const result = enrichMessages(messages)
+    expect(result).toHaveLength(3)
+    expect(result.map(m => m.eventType)).toEqual(['user', 'tool_use', 'lifecycle'])
+  })
+
+  it('looks back up to 3 positions for a system event', () => {
+    const messages = [
+      makeMsg({
+        eventType: 'system',
+        payload: JSON.stringify({
+          value: { last_assistant_message: 'Found it' },
+        }),
+      }),
+      makeMsg({ eventType: 'user', payload: 'filler1' }),
+      makeMsg({ eventType: 'user', payload: 'filler2' }),
+      makeMsg({ eventType: 'assistant', payload: '' }),
+    ]
+
+    const result = enrichMessages(messages)
+    const assistant = result.find(m => m.eventType === 'assistant')
+    expect(assistant).toBeDefined()
+    expect(assistant!.payload).toBe('Found it')
+  })
+
+  it('does not look back more than 3 positions', () => {
+    const messages = [
+      makeMsg({
+        eventType: 'system',
+        payload: JSON.stringify({
+          value: { last_assistant_message: 'Too far' },
+        }),
+      }),
+      makeMsg({ eventType: 'user', payload: 'a' }),
+      makeMsg({ eventType: 'user', payload: 'b' }),
+      makeMsg({ eventType: 'user', payload: 'c' }),
+      makeMsg({ eventType: 'assistant', payload: '' }),
+    ]
+
+    const result = enrichMessages(messages)
+    // The empty assistant should be dropped since system event is 4 positions back
+    const assistant = result.find(m => m.eventType === 'assistant')
+    expect(assistant).toBeUndefined()
+  })
+})
+
+// ---- groupChatItems ----
+
+describe('groupChatItems', () => {
+  it('groups a tool_use followed by a matching tool_result', () => {
+    const toolCallId = 'tc-pair-1'
+    const messages = [
+      makeMsg({
+        eventType: 'tool_use',
+        payload: JSON.stringify({ tool: 'Read', tool_call_id: toolCallId }),
+      }),
+      makeMsg({
+        eventType: 'tool_result',
+        payload: JSON.stringify({ tool_call_id: toolCallId, result: 'file contents' }),
+      }),
+    ]
+
+    const items = groupChatItems(messages)
+    expect(items).toHaveLength(1)
+    expect(items[0].kind).toBe('tool_call')
+    if (items[0].kind === 'tool_call') {
+      expect(items[0].group.toolUse.eventType).toBe('tool_use')
+      expect(items[0].group.toolResult).not.toBeNull()
+      expect(items[0].group.toolResult!.eventType).toBe('tool_result')
+    }
+  })
+
+  it('treats tool_result with no matching tool_use as a standalone message', () => {
+    const messages = [
+      makeMsg({
+        eventType: 'tool_result',
+        payload: JSON.stringify({ tool_call_id: 'orphan-id', result: 'data' }),
+      }),
+    ]
+
+    const items = groupChatItems(messages)
+    expect(items).toHaveLength(1)
+    expect(items[0].kind).toBe('message')
+  })
+
+  it('wraps user and assistant messages as message items', () => {
+    const messages = [
+      makeMsg({ eventType: 'user', payload: 'hi' }),
+      makeMsg({ eventType: 'assistant', payload: 'hello' }),
+    ]
+
+    const items = groupChatItems(messages)
+    expect(items).toHaveLength(2)
+    expect(items[0].kind).toBe('message')
+    expect(items[1].kind).toBe('message')
+    if (items[0].kind === 'message') {
+      expect(items[0].message.eventType).toBe('user')
+    }
+    if (items[1].kind === 'message') {
+      expect(items[1].message.eventType).toBe('assistant')
+    }
+  })
+
+  it('pairs multiple concurrent tool calls correctly', () => {
+    const messages = [
+      makeMsg({
+        eventType: 'tool_use',
+        payload: JSON.stringify({ tool: 'Read', tool_call_id: 'tc-a' }),
+      }),
+      makeMsg({
+        eventType: 'tool_use',
+        payload: JSON.stringify({ tool: 'Bash', tool_call_id: 'tc-b' }),
+      }),
+      makeMsg({
+        eventType: 'tool_result',
+        payload: JSON.stringify({ tool_call_id: 'tc-b', result: 'bash output' }),
+      }),
+      makeMsg({
+        eventType: 'tool_result',
+        payload: JSON.stringify({ tool_call_id: 'tc-a', result: 'file data' }),
+      }),
+    ]
+
+    const items = groupChatItems(messages)
+    expect(items).toHaveLength(2)
+    // Both should be tool_call items
+    expect(items[0].kind).toBe('tool_call')
+    expect(items[1].kind).toBe('tool_call')
+    if (items[0].kind === 'tool_call' && items[1].kind === 'tool_call') {
+      // tc-a was first, tc-b second
+      expect(items[0].group.id).toBe('tc-a')
+      expect(items[0].group.toolResult).not.toBeNull()
+      expect(items[1].group.id).toBe('tc-b')
+      expect(items[1].group.toolResult).not.toBeNull()
+    }
+  })
+
+  it('leaves tool_use without a result as a tool_call with null toolResult', () => {
+    const messages = [
+      makeMsg({
+        eventType: 'tool_use',
+        payload: JSON.stringify({ tool: 'Bash', tool_call_id: 'tc-pending' }),
+      }),
+    ]
+
+    const items = groupChatItems(messages)
+    expect(items).toHaveLength(1)
+    expect(items[0].kind).toBe('tool_call')
+    if (items[0].kind === 'tool_call') {
+      expect(items[0].group.toolResult).toBeNull()
+    }
+  })
+})
+
+// ---- buildChatItems (integration) ----
+
+describe('buildChatItems', () => {
+  it('processes a full conversation flow end-to-end', () => {
+    const messages = [
+      makeMsg({ eventType: 'user', payload: 'Fix the bug' }),
+      makeMsg({ eventType: 'lifecycle', payload: 'session_started' }),
+      makeMsg({
+        eventType: 'system',
+        payload: JSON.stringify({
+          value: { last_assistant_message: 'I will fix the bug.' },
+        }),
+      }),
+      makeMsg({ eventType: 'assistant', payload: '' }),
+      makeMsg({
+        eventType: 'tool_use',
+        payload: JSON.stringify({ tool: 'Read', tool_call_id: 'tc-build' }),
+      }),
+      makeMsg({
+        eventType: 'tool_result',
+        payload: JSON.stringify({ tool_call_id: 'tc-build', result: 'src code' }),
+      }),
+      makeMsg({ eventType: 'assistant', payload: 'Done fixing.' }),
+    ]
+
+    const items = buildChatItems(messages)
+
+    // lifecycle and system events are filtered out
+    const kinds = items.map(i => i.kind)
+    expect(kinds).toEqual(['message', 'message', 'tool_call', 'message'])
+
+    // First message is the user message
+    if (items[0].kind === 'message') {
+      expect(items[0].message.eventType).toBe('user')
+      expect(items[0].message.payload).toBe('Fix the bug')
+    }
+
+    // Second message is the enriched assistant
+    if (items[1].kind === 'message') {
+      expect(items[1].message.eventType).toBe('assistant')
+      expect(items[1].message.payload).toBe('I will fix the bug.')
+    }
+
+    // Tool call is grouped
+    if (items[2].kind === 'tool_call') {
+      expect(items[2].group.toolResult).not.toBeNull()
+    }
+
+    // Final assistant message
+    if (items[3].kind === 'message') {
+      expect(items[3].message.eventType).toBe('assistant')
+      expect(items[3].message.payload).toBe('Done fixing.')
+    }
+  })
+
+  it('filters out lifecycle and system events from chat items', () => {
+    const messages = [
+      makeMsg({ eventType: 'lifecycle', payload: 'created' }),
+      makeMsg({ eventType: 'system', payload: '{}' }),
+      makeMsg({ eventType: 'user', payload: 'hello' }),
+    ]
+
+    const items = buildChatItems(messages)
+    expect(items).toHaveLength(1)
+    if (items[0].kind === 'message') {
+      expect(items[0].message.eventType).toBe('user')
+    }
+  })
+
+  it('includes enriched empty assistant messages derived from system events', () => {
+    const messages = [
+      makeMsg({
+        eventType: 'system',
+        payload: JSON.stringify({
+          value: { last_assistant_message: 'Enriched reply' },
+        }),
+      }),
+      makeMsg({ eventType: 'assistant', payload: '' }),
+    ]
+
+    const items = buildChatItems(messages)
+    expect(items).toHaveLength(1)
+    if (items[0].kind === 'message') {
+      expect(items[0].message.eventType).toBe('assistant')
+      expect(items[0].message.payload).toBe('Enriched reply')
+    }
+  })
+
+  it('returns empty array when given no messages', () => {
+    expect(buildChatItems([])).toEqual([])
+  })
+})
diff --git a/components/ambient-ui/src/components/chat-messages.tsx b/components/ambient-ui/src/components/chat-messages.tsx
new file mode 100644
index 000000000..4d987bf7f
--- /dev/null
+++ b/components/ambient-ui/src/components/chat-messages.tsx
@@ -0,0 +1,480 @@
+'use client'
+
+import { useState, useCallback, useRef } from 'react'
+import ReactMarkdown from 'react-markdown'
+import remarkGfm from 'remark-gfm'
+import { User, Bot, Wrench, Send, ChevronDown, ChevronRight } from 'lucide-react'
+import { Button } from '@/components/ui/button'
+import { Textarea } from '@/components/ui/textarea'
+import { Skeleton } from '@/components/ui/skeleton'
+import { Badge } from '@/components/ui/badge'
+import type { DomainSessionMessage, SessionEventType } from '@/domain/types'
+import { useSendMessage } from '@/queries/use-send-message'
+import { formatRelativeTime } from '@/lib/format-timestamp'
+import { cn } from '@/lib/utils'
+
+// ---- Constants ----
+
+export const CHAT_EVENT_TYPES: ReadonlySet<SessionEventType> = new Set([
+  'user',
+  'assistant',
+  'tool_use',
+  'tool_result',
+])
+
+// ---- Payload Parsing Helpers ----
+
+type ToolPayload = {
+  name: string
+  arguments: Record<string, unknown>
+}
+
+export function tryParseToolPayload(payload: string): ToolPayload | null {
+  try {
+    const parsed: unknown = JSON.parse(payload)
+    if (typeof parsed !== 'object' || parsed === null || Array.isArray(parsed)) {
+      return null
+    }
+    const obj = parsed as Record<string, unknown>
+    const name =
+      typeof obj.tool === 'string' ? obj.tool :
+      typeof obj.name === 'string' ? obj.name : null
+    if (!name) return null
+
+    const args =
+      typeof obj.arguments === 'object' && obj.arguments !== null && !Array.isArray(obj.arguments)
+        ? (obj.arguments as Record<string, unknown>)
+        : typeof obj.input === 'object' && obj.input !== null && !Array.isArray(obj.input)
+          ? (obj.input as Record<string, unknown>)
+          : {}
+
+    return { name, arguments: args }
+  } catch {
+    return null
+  }
+}
+
+type ToolResultPayload = {
+  result: string
+  toolCallId: string
+}
+
+export function tryParseToolResult(payload: string): ToolResultPayload | null {
+  try {
+    const parsed: unknown = JSON.parse(payload)
+    if (typeof parsed !== 'object' || parsed === null || Array.isArray(parsed)) {
+      return null
+    }
+    const obj = parsed as Record<string, unknown>
+    let result = typeof obj.result === 'string' ? obj.result : payload
+    if (result.startsWith('"') && result.endsWith('"')) {
+      result = result.slice(1, -1)
+    }
+    return {
+      result,
+      toolCallId: typeof obj.tool_call_id === 'string' ? obj.tool_call_id : '',
+    }
+  } catch {
+    return null
+  }
+}
+
+export function tryFormatJson(payload: string): string {
+  try {
+    const parsed: unknown = JSON.parse(payload)
+    return JSON.stringify(parsed, null, 2)
+  } catch {
+    return payload
+  }
+}
+
+// ---- Message Enrichment ----
+
+export function extractLastAssistantMessage(payload: string): string | null {
+  try {
+    const parsed: unknown = JSON.parse(payload)
+    if (typeof parsed !== 'object' || parsed === null || Array.isArray(parsed)) return null
+    const obj = parsed as Record<string, unknown>
+    if (typeof obj.value !== 'object' || obj.value === null) return null
+    const value = obj.value as Record<string, unknown>
+    if (typeof value.last_assistant_message === 'string' && value.last_assistant_message.trim()) {
+      return value.last_assistant_message
+    }
+    return null
+  } catch {
+    return null
+  }
+}
+
+export function enrichMessages(messages: DomainSessionMessage[]): DomainSessionMessage[] {
+  const enriched: DomainSessionMessage[] = []
+  for (let i = 0; i < messages.length; i++) {
+    const msg = messages[i]
+    if (msg.eventType === 'assistant' && !msg.payload.trim()) {
+      for (let j = i - 1; j >= Math.max(0, i - 3); j--) {
+        if (messages[j].eventType === 'system') {
+          const extracted = extractLastAssistantMessage(messages[j].payload)
+          if (extracted) {
+            enriched.push({ ...msg, payload: extracted })
+            break
+          }
+        }
+      }
+      // Empty assistant messages with no extractable text are dropped — the
+      // runner sometimes pushes an empty "assistant" record alongside a system
+      // event that contains the actual response in last_assistant_message.
+      continue
+    }
+    enriched.push(msg)
+  }
+  return enriched
+}
+
+// ---- Tool Call Grouping ----
+
+export type ToolCallGroup = {
+  id: string
+  toolUse: DomainSessionMessage
+  toolResult: DomainSessionMessage | null
+}
+
+export type ChatItem =
+  | { kind: 'message'; message: DomainSessionMessage }
+  | { kind: 'tool_call'; group: ToolCallGroup }
+
+export function groupChatItems(messages: DomainSessionMessage[]): ChatItem[] {
+  const items: ChatItem[] = []
+  const pendingToolUses = new Map<string, ToolCallGroup>()
+
+  for (const msg of messages) {
+    if (msg.eventType === 'tool_use') {
+      const toolPayload = tryParseToolPayload(msg.payload)
+      let toolCallId = msg.id
+      if (toolPayload) {
+        try {
+          const raw = JSON.parse(msg.payload) as Record<string, unknown>
+          if (typeof raw.tool_call_id === 'string') {
+            toolCallId = raw.tool_call_id
+          }
+        } catch {
+          // use msg.id as fallback
+        }
+      }
+      const group: ToolCallGroup = { id: toolCallId, toolUse: msg, toolResult: null }
+      pendingToolUses.set(toolCallId, group)
+      items.push({ kind: 'tool_call', group })
+    } else if (msg.eventType === 'tool_result') {
+      const resultParsed = tryParseToolResult(msg.payload)
+      const toolCallId = resultParsed?.toolCallId
+      if (toolCallId && pendingToolUses.has(toolCallId)) {
+        pendingToolUses.get(toolCallId)!.toolResult = msg
+      } else {
+        items.push({ kind: 'message', message: msg })
+      }
+    } else {
+      items.push({ kind: 'message', message: msg })
+    }
+  }
+  return items
+}
+
+// ---- Message Bubble Components ----
+
+export function UserMessage({ message }: { message: DomainSessionMessage }) {
+  return (
+    <article
+      aria-label={`User message, ${formatRelativeTime(message.createdAt)}`}
+      className="flex gap-3 px-4 py-3"
+    >
+      <div className="flex h-7 w-7 shrink-0 items-center justify-center rounded-full bg-primary/10">
+        <User className="h-4 w-4 text-primary" aria-hidden="true" />
+      </div>
+      <div className="min-w-0 flex-1">
+        <div className="flex items-center gap-2 mb-1">
+          <span className="text-sm font-medium">You</span>
+          <span className="text-xs text-muted-foreground">
+            {formatRelativeTime(message.createdAt)}
+          </span>
+        </div>
+        <div className="rounded-lg bg-primary/10 px-3 py-2 text-sm text-foreground prose prose-sm dark:prose-invert max-w-none prose-pre:bg-muted prose-pre:text-foreground prose-code:text-foreground">
+          <ReactMarkdown remarkPlugins={[remarkGfm]}>
+            {message.payload}
+          </ReactMarkdown>
+        </div>
+      </div>
+    </article>
+  )
+}
+
+export function AssistantMessage({ message }: { message: DomainSessionMessage }) {
+  return (
+    <article
+      aria-label={`Assistant message, ${formatRelativeTime(message.createdAt)}`}
+      className="flex gap-3 px-4 py-3"
+    >
+      <div className="flex h-7 w-7 shrink-0 items-center justify-center rounded-full bg-secondary">
+        <Bot className="h-4 w-4 text-secondary-foreground" aria-hidden="true" />
+      </div>
+      <div className="min-w-0 flex-1">
+        <div className="flex items-center gap-2 mb-1">
+          <span className="text-sm font-medium">Assistant</span>
+          <span className="text-xs text-muted-foreground">
+            {formatRelativeTime(message.createdAt)}
+          </span>
+        </div>
+        <div className="rounded-lg bg-muted/50 px-3 py-2 text-sm text-foreground prose prose-sm dark:prose-invert max-w-none prose-pre:bg-muted prose-pre:text-foreground prose-code:text-foreground">
+          <ReactMarkdown remarkPlugins={[remarkGfm]}>
+            {message.payload}
+          </ReactMarkdown>
+        </div>
+      </div>
+    </article>
+  )
+}
+
+export function ToolCallBlock({ group }: { group: ToolCallGroup }) {
+  const [expanded, setExpanded] = useState(false)
+  const toolPayload = tryParseToolPayload(group.toolUse.payload)
+  const toolName = toolPayload?.name ?? 'Tool Call'
+  const hasArgs = Object.keys(toolPayload?.arguments ?? {}).length > 0
+  const argsText = toolPayload
+    ? JSON.stringify(toolPayload.arguments, null, 2)
+    : tryFormatJson(group.toolUse.payload)
+
+  const resultParsed = group.toolResult ? tryParseToolResult(group.toolResult.payload) : null
+  const resultText = resultParsed ? resultParsed.result : group.toolResult ? tryFormatJson(group.toolResult.payload) : null
+
+  return (
+    <article
+      aria-label={`Tool call: ${toolName}, ${formatRelativeTime(group.toolUse.createdAt)}`}
+      className="flex gap-3 px-4 py-2"
+    >
+      <div className="flex h-7 w-7 shrink-0 items-center justify-center rounded-full bg-muted">
+        <Wrench className="h-4 w-4 text-muted-foreground" aria-hidden="true" />
+      </div>
+      <div className="min-w-0 flex-1">
+        <button
+          type="button"
+          className="flex items-center gap-1.5 text-sm text-muted-foreground hover:text-foreground transition-colors"
+          onClick={() => setExpanded(prev => !prev)}
+          aria-expanded={expanded}
+        >
+          {expanded ? (
+            <ChevronDown className="h-3.5 w-3.5" aria-hidden="true" />
+          ) : (
+            <ChevronRight className="h-3.5 w-3.5" aria-hidden="true" />
+          )}
+          <span className="font-mono text-xs font-medium text-foreground">{toolName}</span>
+          {resultText && !expanded && (
+            <span className="text-xs text-muted-foreground truncate max-w-[300px]">
+              — {resultText.slice(0, 60)}{resultText.length > 60 ? '...' : ''}
+            </span>
+          )}
+        </button>
+        {expanded && (
+          <div className="mt-1.5 space-y-1.5">
+            {hasArgs && (
+              <div className="rounded-md border border-border bg-muted/50 p-2">
+                <div className="mb-1 text-[10px] font-medium uppercase tracking-wider text-muted-foreground">
+                  Arguments
+                </div>
+                <pre className="whitespace-pre-wrap break-words font-mono text-xs text-foreground max-h-[200px] overflow-y-auto">
+                  {argsText}
+                </pre>
+              </div>
+            )}
+            {resultText && (
+              <div className="rounded-md border border-border bg-muted/50 p-2 border-l-2 border-l-primary/30">
+                <div className="mb-1 text-[10px] font-medium uppercase tracking-wider text-muted-foreground">
+                  Result
+                </div>
+                <pre className="whitespace-pre-wrap break-words font-mono text-xs text-foreground max-h-[300px] overflow-y-auto">
+                  {resultText}
+                </pre>
+              </div>
+            )}
+          </div>
+        )}
+      </div>
+    </article>
+  )
+}
+
+function SimpleChatMessage({ message }: { message: DomainSessionMessage }) {
+  switch (message.eventType) {
+    case 'user':
+      return <UserMessage message={message} />
+    case 'assistant':
+      return <AssistantMessage message={message} />
+    default:
+      return null
+  }
+}
+
+// ---- Phase Status Indicator ----
+
+const PHASE_STYLES: Record<string, string> = {
+  Running: 'bg-emerald-100 text-emerald-800 border-emerald-300',
+  Pending: 'bg-yellow-100 text-yellow-800 border-yellow-300',
+  Creating: 'bg-blue-100 text-blue-800 border-blue-300',
+  Stopping: 'bg-orange-100 text-orange-800 border-orange-300',
+  Completed: 'bg-[#f2f2f2] text-[#4d4d4d] border-[#e0e0e0]',
+  Failed: 'bg-[#ffe3d9] text-[#731f00] border-[#fbbea8]',
+  Stopped: 'bg-[#f2f2f2] text-[#4d4d4d] border-[#e0e0e0]',
+}
+
+export function PhaseIndicator({ phase }: { phase: string }) {
+  const style = PHASE_STYLES[phase] ?? PHASE_STYLES.Stopped
+  return (
+    <Badge
+      variant="outline"
+      className={cn('text-[11px] font-medium', style)}
+    >
+      {phase}
+    </Badge>
+  )
+}
+
+// ---- Chat Input ----
+
+type ChatInputProps = {
+  sessionId: string
+  phase: string
+  disabled: boolean
+}
+
+export function ChatInput({ sessionId, phase, disabled }: ChatInputProps) {
+  const [input, setInput] = useState('')
+  const textareaRef = useRef<HTMLTextAreaElement | null>(null)
+  const sendMessage = useSendMessage(sessionId)
+  const isRunning = phase === 'Running'
+  const canSend = isRunning && !disabled && input.trim().length > 0 && !sendMessage.isPending
+
+  const handleSend = useCallback(() => {
+    const trimmed = input.trim()
+    if (!trimmed || !isRunning || disabled || sendMessage.isPending) return
+    sendMessage.mutate(trimmed, {
+      onSuccess: () => {
+        setInput('')
+        textareaRef.current?.focus()
+      },
+    })
+  }, [input, isRunning, sendMessage])
+
+  const handleKeyDown = useCallback(
+    (e: React.KeyboardEvent<HTMLTextAreaElement>) => {
+      if (e.key === 'Enter' && !e.shiftKey) {
+        e.preventDefault()
+        handleSend()
+      }
+    },
+    [handleSend],
+  )
+
+  return (
+    <div className="border-t bg-background px-4 py-3">
+      {!isRunning && (
+        <div className="flex items-center gap-2 mb-2">
+          <span className="text-xs text-muted-foreground">
+            Send is disabled while the session is not running.
+          </span>
+        </div>
+      )}
+      {sendMessage.isError && (
+        <div className="mb-2">
+          <span className="text-xs text-destructive">
+            Failed to send message. Please try again.
+          </span>
+        </div>
+      )}
+      <div className="flex gap-2">
+        <Textarea
+          ref={textareaRef}
+          value={input}
+          onChange={e => setInput(e.target.value)}
+          onKeyDown={handleKeyDown}
+          placeholder={isRunning ? 'Send a message...' : 'Session is not running'}
+          disabled={!isRunning || sendMessage.isPending}
+          className="min-h-[40px] max-h-[120px] resize-none"
+          aria-label="Chat message input"
+          rows={1}
+        />
+        <Button
+          onClick={handleSend}
+          disabled={!canSend}
+          size="icon"
+          aria-label="Send message"
+          className="shrink-0 self-end"
+        >
+          <Send className="h-4 w-4" />
+        </Button>
+      </div>
+      {isRunning && (
+        <p className="text-[10px] text-muted-foreground mt-1">
+          Enter to send · Shift+Enter for new line
+        </p>
+      )}
+    </div>
+  )
+}
+
+// ---- Chat Items List (shared between tab and sidebar) ----
+
+export function ChatItemsList({
+  items,
+  isLoading,
+}: {
+  items: ChatItem[]
+  isLoading: boolean
+}) {
+  if (isLoading) {
+    return (
+      <div className="space-y-4 p-4">
+        <div className="flex gap-3">
+          <Skeleton className="h-7 w-7 rounded-full" />
+          <div className="space-y-2 flex-1">
+            <Skeleton className="h-4 w-20" />
+            <Skeleton className="h-16 w-3/4 rounded-lg" />
+          </div>
+        </div>
+        <div className="flex gap-3">
+          <Skeleton className="h-7 w-7 rounded-full" />
+          <div className="space-y-2 flex-1">
+            <Skeleton className="h-4 w-24" />
+            <Skeleton className="h-24 w-full rounded-lg" />
+          </div>
+        </div>
+      </div>
+    )
+  }
+
+  if (items.length === 0) {
+    return (
+      <div className="flex flex-col items-center justify-center py-16 text-muted-foreground">
+        <Bot className="h-10 w-10 mb-3 opacity-40" aria-hidden="true" />
+        <p className="text-sm">No conversation messages yet.</p>
+        <p className="text-xs mt-1">
+          Messages will appear here as the session runs.
+        </p>
+      </div>
+    )
+  }
+
+  return (
+    <div className="divide-y divide-transparent">
+      {items.map(item => {
+        if (item.kind === 'tool_call') {
+          return <ToolCallBlock key={item.group.id} group={item.group} />
+        }
+        return <SimpleChatMessage key={item.message.id} message={item.message} />
+      })}
+    </div>
+  )
+}
+
+/** Filter and group raw messages into chat items */
+export function buildChatItems(messages: DomainSessionMessage[]): ChatItem[] {
+  const enriched = enrichMessages(messages)
+  const chatOnly = enriched.filter(m => CHAT_EVENT_TYPES.has(m.eventType))
+  return groupChatItems(chatOnly)
+}
diff --git a/components/ambient-ui/src/components/chat-sidebar-context.tsx b/components/ambient-ui/src/components/chat-sidebar-context.tsx
new file mode 100644
index 000000000..08c022ab5
--- /dev/null
+++ b/components/ambient-ui/src/components/chat-sidebar-context.tsx
@@ -0,0 +1,79 @@
+'use client'
+
+import {
+  createContext,
+  useContext,
+  useState,
+  useCallback,
+  useEffect,
+  useMemo,
+  type ReactNode,
+} from 'react'
+
+type ChatSidebarState = {
+  openSessionId: string | null
+  isOpen: boolean
+  openSidebar: (sessionId: string) => void
+  closeSidebar: () => void
+}
+
+const ChatSidebarContext = createContext<ChatSidebarState | null>(null)
+
+function readChatParam(): string | null {
+  if (typeof window === 'undefined') return null
+  return new URL(window.location.href).searchParams.get('chat')
+}
+
+function updateChatParam(sessionId: string | null) {
+  const url = new URL(window.location.href)
+  if (sessionId) {
+    url.searchParams.set('chat', sessionId)
+  } else {
+    url.searchParams.delete('chat')
+  }
+  window.history.replaceState({}, '', url.toString())
+}
+
+export function ChatSidebarProvider({ children }: { children: ReactNode }) {
+  const [openSessionId, setOpenSessionId] = useState<string | null>(readChatParam)
+
+  const openSidebar = useCallback((sessionId: string) => {
+    setOpenSessionId(sessionId)
+    updateChatParam(sessionId)
+  }, [])
+
+  const closeSidebar = useCallback(() => {
+    setOpenSessionId(null)
+    updateChatParam(null)
+  }, [])
+
+  useEffect(() => {
+    const handlePopState = () => setOpenSessionId(readChatParam())
+    window.addEventListener('popstate', handlePopState)
+    return () => window.removeEventListener('popstate', handlePopState)
+  }, [])
+
+  const value = useMemo<ChatSidebarState>(
+    () => ({
+      openSessionId,
+      isOpen: openSessionId !== null,
+      openSidebar,
+      closeSidebar,
+    }),
+    [openSessionId, openSidebar, closeSidebar],
+  )
+
+  return (
+    <ChatSidebarContext.Provider value={value}>
+      {children}
+    </ChatSidebarContext.Provider>
+  )
+}
+
+export function useChatSidebar(): ChatSidebarState {
+  const ctx = useContext(ChatSidebarContext)
+  if (!ctx) {
+    throw new Error('useChatSidebar must be used within a ChatSidebarProvider')
+  }
+  return ctx
+}
diff --git a/components/ambient-ui/src/components/chat-sidebar.tsx b/components/ambient-ui/src/components/chat-sidebar.tsx
new file mode 100644
index 000000000..533753366
--- /dev/null
+++ b/components/ambient-ui/src/components/chat-sidebar.tsx
@@ -0,0 +1,303 @@
+'use client'
+
+import { useRef, useEffect, useState, useCallback, useMemo } from 'react'
+import { useRouter } from 'next/navigation'
+import { X, PanelRightClose, PanelRightOpen, GripVertical, ChevronUp, ChevronDown } from 'lucide-react'
+import { Button } from '@/components/ui/button'
+import { Tooltip, TooltipContent, TooltipProvider, TooltipTrigger } from '@/components/ui/tooltip'
+import { useChatSidebar } from '@/components/chat-sidebar-context'
+import {
+  ChatItemsList,
+  ChatInput,
+  buildChatItems,
+  PhaseIndicator,
+} from '@/components/chat-messages'
+import { useSession } from '@/queries/use-sessions'
+import { useSessionMessages } from '@/queries/use-session-messages'
+import { useLiveTail, LiveIndicator } from '@/app/(dashboard)/[projectId]/fleet/[sessionId]/_components/live-tail-indicator'
+
+const MIN_WIDTH = 320
+const MAX_WIDTH = 800
+const DEFAULT_WIDTH = 420
+const COLLAPSED_WIDTH = 40
+
+export function ChatSidebar() {
+  const { openSessionId, isOpen, closeSidebar } = useChatSidebar()
+  const router = useRouter()
+  const [collapsed, setCollapsed] = useState(false)
+  const [width, setWidth] = useState(DEFAULT_WIDTH)
+  const [showScrollToTop, setShowScrollToTop] = useState(false)
+  const isDragging = useRef(false)
+  const startX = useRef(0)
+  const startWidth = useRef(DEFAULT_WIDTH)
+
+  const { data: session } = useSession(openSessionId ?? '', undefined)
+  const { data: messagesData, isLoading: messagesLoading } = useSessionMessages(
+    openSessionId ?? '',
+  )
+
+  const chatItems = useMemo(() => {
+    return buildChatItems(messagesData?.items ?? [])
+  }, [messagesData])
+
+  const { scrollRef, sentinelRef, isAtBottom, newEventCount, scrollToBottom } =
+    useLiveTail(chatItems.length)
+
+  const [scrolledUp, setScrolledUp] = useState(false)
+
+  const handleScroll = useCallback(() => {
+    const container = scrollRef.current
+    if (!container) return
+    setShowScrollToTop(container.scrollTop > 300)
+    const atBottom = container.scrollHeight - container.scrollTop - container.clientHeight < 50
+    setScrolledUp(!atBottom)
+  }, [scrollRef])
+
+  const scrollToTop = useCallback(() => {
+    scrollRef.current?.scrollTo({ top: 0, behavior: 'smooth' })
+  }, [scrollRef])
+
+  // Auto-scroll on initial load
+  const hasScrolledOnLoad = useRef(false)
+  useEffect(() => {
+    if (!messagesLoading && chatItems.length > 0 && !hasScrolledOnLoad.current) {
+      hasScrolledOnLoad.current = true
+      requestAnimationFrame(() => {
+        scrollToBottom()
+      })
+    }
+  }, [messagesLoading, chatItems.length, scrollToBottom])
+
+  // Reset scroll tracking when session changes
+  useEffect(() => {
+    hasScrolledOnLoad.current = false
+  }, [openSessionId])
+
+  // Drag-to-resize handler with cleanup refs
+  const dragListenersRef = useRef<{ move: (e: MouseEvent) => void; up: () => void } | null>(null)
+
+  const cleanupDrag = useCallback(() => {
+    if (dragListenersRef.current) {
+      document.removeEventListener('mousemove', dragListenersRef.current.move)
+      document.removeEventListener('mouseup', dragListenersRef.current.up)
+      dragListenersRef.current = null
+    }
+    isDragging.current = false
+    document.body.style.cursor = ''
+    document.body.style.userSelect = ''
+  }, [])
+
+  useEffect(() => {
+    return cleanupDrag
+  }, [cleanupDrag])
+
+  const handleMouseDown = useCallback(
+    (e: React.MouseEvent) => {
+      e.preventDefault()
+      cleanupDrag()
+      isDragging.current = true
+      startX.current = e.clientX
+      startWidth.current = width
+      document.body.style.cursor = 'col-resize'
+      document.body.style.userSelect = 'none'
+
+      const handleMouseMove = (ev: MouseEvent) => {
+        if (!isDragging.current) return
+        const delta = startX.current - ev.clientX
+        const newWidth = Math.min(MAX_WIDTH, Math.max(MIN_WIDTH, startWidth.current + delta))
+        setWidth(newWidth)
+      }
+
+      const handleMouseUp = () => cleanupDrag()
+
+      dragListenersRef.current = { move: handleMouseMove, up: handleMouseUp }
+      document.addEventListener('mousemove', handleMouseMove)
+      document.addEventListener('mouseup', handleMouseUp)
+    },
+    [width, cleanupDrag],
+  )
+
+  // Handle Escape key to close
+  useEffect(() => {
+    if (!isOpen) return
+    const handleKeyDown = (e: KeyboardEvent) => {
+      if (e.key === 'Escape') {
+        closeSidebar()
+      }
+    }
+    document.addEventListener('keydown', handleKeyDown)
+    return () => document.removeEventListener('keydown', handleKeyDown)
+  }, [isOpen, closeSidebar])
+
+  if (!isOpen || !openSessionId) return null
+
+  const sessionName = session?.name ?? 'Loading...'
+  const sessionPhase = session?.phase ?? 'Pending'
+
+  if (collapsed) {
+    return (
+      <aside
+        className="flex-shrink-0 border-l bg-background flex flex-col items-center py-3 gap-2 h-screen sticky top-0"
+        style={{ width: COLLAPSED_WIDTH }}
+        aria-label="Chat sidebar (collapsed)"
+      >
+        <Button
+          variant="ghost"
+          size="icon"
+          className="h-8 w-8"
+          onClick={() => setCollapsed(false)}
+          aria-label="Expand chat sidebar"
+        >
+          <PanelRightOpen className="h-4 w-4" />
+        </Button>
+        <div className="flex-1 flex items-center">
+          <span
+            className="text-xs font-medium text-muted-foreground [writing-mode:vertical-lr] rotate-180 truncate max-h-48"
+            title={sessionName}
+          >
+            {sessionName}
+          </span>
+        </div>
+      </aside>
+    )
+  }
+
+  return (
+    <aside
+      className="flex-shrink-0 border-l bg-background flex flex-col relative h-screen sticky top-0 z-20 max-md:!w-screen max-md:fixed max-md:inset-0 max-md:border-l-0"
+      style={{ width }}
+      aria-label={`Chat sidebar for session ${sessionName}`}
+      role="complementary"
+    >
+      {/* Drag handle (left edge) */}
+      <div
+        className="absolute inset-y-0 left-0 w-1 cursor-col-resize hover:bg-primary/20 active:bg-primary/30 z-10 flex items-center"
+        onMouseDown={handleMouseDown}
+        role="separator"
+        aria-orientation="vertical"
+        aria-label="Resize chat sidebar"
+        tabIndex={0}
+        onKeyDown={(e) => {
+          if (e.key === 'ArrowLeft') {
+            setWidth(w => Math.min(MAX_WIDTH, w + 20))
+          } else if (e.key === 'ArrowRight') {
+            setWidth(w => Math.max(MIN_WIDTH, w - 20))
+          }
+        }}
+      >
+        <GripVertical className="h-4 w-4 text-muted-foreground/50 -ml-1.5 pointer-events-none" aria-hidden="true" />
+      </div>
+
+      {/* Header */}
+      <div className="flex items-center gap-2 border-b px-3 py-2 min-h-[48px]">
+        <button
+          type="button"
+          className="flex-1 min-w-0 text-left cursor-pointer hover:opacity-80 transition-opacity"
+          onClick={() => {
+            const projectId = session?.projectId
+            if (projectId && openSessionId) {
+              router.push(`/${projectId}/fleet/${openSessionId}`)
+            }
+          }}
+          title="Go to session detail"
+        >
+          <div className="flex items-center gap-2">
+            <span className="text-sm font-semibold truncate" title={sessionName}>
+              {sessionName}
+            </span>
+            <PhaseIndicator phase={sessionPhase} />
+          </div>
+        </button>
+        <div className="flex items-center gap-1">
+          <Button
+            variant="ghost"
+            size="icon"
+            className="h-7 w-7"
+            onClick={() => setCollapsed(true)}
+            aria-label="Collapse chat sidebar"
+          >
+            <PanelRightClose className="h-4 w-4" />
+          </Button>
+          <Button
+            variant="ghost"
+            size="icon"
+            className="h-7 w-7"
+            onClick={closeSidebar}
+            aria-label="Close chat sidebar"
+          >
+            <X className="h-4 w-4" />
+          </Button>
+        </div>
+      </div>
+
+      {/* Message area */}
+      <div className="flex-1 min-h-0 overflow-hidden relative">
+        {isAtBottom && chatItems.length > 0 && (
+          <div className="absolute top-2 right-3 z-10">
+            <LiveIndicator />
+          </div>
+        )}
+        <div
+          ref={scrollRef}
+          className="h-full overflow-y-auto"
+          role="log"
+          aria-label="Chat messages"
+          onScroll={handleScroll}
+        >
+          <ChatItemsList items={chatItems} isLoading={messagesLoading} />
+          <div ref={sentinelRef} className="h-1" aria-hidden="true" />
+        </div>
+
+        {/* Scroll buttons */}
+        <TooltipProvider>
+          <div className="absolute bottom-3 right-3 z-10 flex flex-col gap-1">
+            <div className={`transition-all duration-200 ${showScrollToTop ? 'opacity-100 scale-100' : 'opacity-0 scale-75 pointer-events-none'}`}>
+              <Tooltip>
+                <TooltipTrigger asChild>
+                  <Button
+                    variant="outline"
+                    size="icon"
+                    className="h-7 w-7 rounded-full shadow-md cursor-pointer"
+                    onClick={scrollToTop}
+                    aria-label="Scroll to top"
+                  >
+                    <ChevronUp className="h-4 w-4" />
+                  </Button>
+                </TooltipTrigger>
+                <TooltipContent side="left">Scroll to top</TooltipContent>
+              </Tooltip>
+            </div>
+            <div className={`transition-all duration-200 ${scrolledUp && chatItems.length > 0 ? 'opacity-100 scale-100' : 'opacity-0 scale-75 pointer-events-none'}`}>
+              <Tooltip>
+                <TooltipTrigger asChild>
+                  <Button
+                    variant="outline"
+                    size="icon"
+                    className="h-7 w-7 rounded-full shadow-md cursor-pointer"
+                    onClick={scrollToBottom}
+                    aria-label="Scroll to bottom"
+                  >
+                    <ChevronDown className="h-4 w-4" />
+                    {newEventCount > 0 && (
+                      <span className="absolute -top-1 -right-1 flex h-4 min-w-4 items-center justify-center rounded-full bg-primary text-[10px] font-bold text-primary-foreground px-1">
+                        {newEventCount}
+                      </span>
+                    )}
+                  </Button>
+                </TooltipTrigger>
+                <TooltipContent side="left">Scroll to bottom</TooltipContent>
+              </Tooltip>
+            </div>
+          </div>
+        </TooltipProvider>
+      </div>
+
+      {/* Input area */}
+      <ChatInput
+        sessionId={openSessionId}
+        phase={sessionPhase}
+        disabled={messagesLoading}
+      />
+    </aside>
+  )
+}
diff --git a/components/ambient-ui/src/components/ui/alert-dialog.tsx b/components/ambient-ui/src/components/ui/alert-dialog.tsx
new file mode 100644
index 000000000..df7f806d7
--- /dev/null
+++ b/components/ambient-ui/src/components/ui/alert-dialog.tsx
@@ -0,0 +1,159 @@
+"use client"
+
+import * as React from "react"
+import * as AlertDialogPrimitive from "@radix-ui/react-alert-dialog"
+
+import { cn } from "@/lib/utils"
+import { buttonVariants } from "@/components/ui/button"
+
+function AlertDialog({
+  ...props
+}: React.ComponentProps<typeof AlertDialogPrimitive.Root>) {
+  return <AlertDialogPrimitive.Root data-slot="alert-dialog" {...props} />
+}
+
+function AlertDialogTrigger({
+  ...props
+}: React.ComponentProps<typeof AlertDialogPrimitive.Trigger>) {
+  return (
+    <AlertDialogPrimitive.Trigger data-slot="alert-dialog-trigger" {...props} />
+  )
+}
+
+function AlertDialogPortal({
+  ...props
+}: React.ComponentProps<typeof AlertDialogPrimitive.Portal>) {
+  return (
+    <AlertDialogPrimitive.Portal data-slot="alert-dialog-portal" {...props} />
+  )
+}
+
+function AlertDialogOverlay({
+  className,
+  ...props
+}: React.ComponentProps<typeof AlertDialogPrimitive.Overlay>) {
+  return (
+    <AlertDialogPrimitive.Overlay
+      data-slot="alert-dialog-overlay"
+      className={cn(
+        "fixed inset-0 z-50 bg-black/50 data-[state=open]:animate-in data-[state=open]:fade-in-0 data-[state=closed]:animate-out data-[state=closed]:fade-out-0",
+        className
+      )}
+      {...props}
+    />
+  )
+}
+
+function AlertDialogContent({
+  className,
+  ...props
+}: React.ComponentProps<typeof AlertDialogPrimitive.Content>) {
+  return (
+    <AlertDialogPortal>
+      <AlertDialogOverlay />
+      <AlertDialogPrimitive.Content
+        data-slot="alert-dialog-content"
+        className={cn(
+          "fixed top-[50%] left-[50%] z-50 grid w-full max-w-[calc(100%-2rem)] translate-x-[-50%] translate-y-[-50%] gap-4 rounded-lg border bg-background p-6 shadow-lg duration-200 sm:max-w-lg data-[state=open]:animate-in data-[state=open]:fade-in-0 data-[state=open]:zoom-in-95 data-[state=closed]:animate-out data-[state=closed]:fade-out-0 data-[state=closed]:zoom-out-95",
+          className
+        )}
+        {...props}
+      />
+    </AlertDialogPortal>
+  )
+}
+
+function AlertDialogHeader({
+  className,
+  ...props
+}: React.ComponentProps<"div">) {
+  return (
+    <div
+      data-slot="alert-dialog-header"
+      className={cn("flex flex-col gap-2 text-center sm:text-left", className)}
+      {...props}
+    />
+  )
+}
+
+function AlertDialogFooter({
+  className,
+  ...props
+}: React.ComponentProps<"div">) {
+  return (
+    <div
+      data-slot="alert-dialog-footer"
+      className={cn(
+        "flex flex-col-reverse gap-2 sm:flex-row sm:justify-end",
+        className
+      )}
+      {...props}
+    />
+  )
+}
+
+function AlertDialogTitle({
+  className,
+  ...props
+}: React.ComponentProps<typeof AlertDialogPrimitive.Title>) {
+  return (
+    <AlertDialogPrimitive.Title
+      data-slot="alert-dialog-title"
+      className={cn("text-lg font-semibold", className)}
+      {...props}
+    />
+  )
+}
+
+function AlertDialogDescription({
+  className,
+  ...props
+}: React.ComponentProps<typeof AlertDialogPrimitive.Description>) {
+  return (
+    <AlertDialogPrimitive.Description
+      data-slot="alert-dialog-description"
+      className={cn("text-sm text-muted-foreground", className)}
+      {...props}
+    />
+  )
+}
+
+function AlertDialogAction({
+  className,
+  ...props
+}: React.ComponentProps<typeof AlertDialogPrimitive.Action>) {
+  return (
+    <AlertDialogPrimitive.Action
+      data-slot="alert-dialog-action"
+      className={cn(buttonVariants(), className)}
+      {...props}
+    />
+  )
+}
+
+function AlertDialogCancel({
+  className,
+  ...props
+}: React.ComponentProps<typeof AlertDialogPrimitive.Cancel>) {
+  return (
+    <AlertDialogPrimitive.Cancel
+      data-slot="alert-dialog-cancel"
+      className={cn(buttonVariants({ variant: "outline" }), className)}
+      {...props}
+    />
+  )
+}
+
+export {
+  AlertDialog,
+  AlertDialogPortal,
+  AlertDialogOverlay,
+  AlertDialogTrigger,
+  AlertDialogContent,
+  AlertDialogHeader,
+  AlertDialogFooter,
+  AlertDialogTitle,
+  AlertDialogDescription,
+  AlertDialogAction,
+  AlertDialogCancel,
+}
diff --git a/components/ambient-ui/src/lib/query-client.ts b/components/ambient-ui/src/lib/query-client.ts
index b0dff3f47..c5b6fa744 100644
--- a/components/ambient-ui/src/lib/query-client.ts
+++ b/components/ambient-ui/src/lib/query-client.ts
@@ -14,11 +14,36 @@ const queryConfig: DefaultOptions = {
   },
 }
 
+function isAuthError(error: unknown): boolean {
+  if (error instanceof Error && error.message.includes('401')) return true
+  if (typeof error === 'object' && error !== null && 'status' in error) {
+    return (error as { status: number }).status === 401
+  }
+  return false
+}
+
+let redirecting = false
+
+function handleAuthError() {
+  if (redirecting || typeof window === 'undefined') return
+  redirecting = true
+  const returnTo = encodeURIComponent(window.location.pathname + window.location.search)
+  window.location.href = `/api/auth/sso/login?returnTo=${returnTo}`
+}
+
 export function makeQueryClient() {
   return new QueryClient({
     defaultOptions: queryConfig,
-    queryCache: new QueryCache(),
-    mutationCache: new MutationCache(),
+    queryCache: new QueryCache({
+      onError: (error) => {
+        if (isAuthError(error)) handleAuthError()
+      },
+    }),
+    mutationCache: new MutationCache({
+      onError: (error) => {
+        if (isAuthError(error)) handleAuthError()
+      },
+    }),
   })
 }
 
diff --git a/components/ambient-ui/src/ports/sessions.ts b/components/ambient-ui/src/ports/sessions.ts
index 8ca0242c0..397ec27d9 100644
--- a/components/ambient-ui/src/ports/sessions.ts
+++ b/components/ambient-ui/src/ports/sessions.ts
@@ -5,4 +5,5 @@ export type SessionsPort = {
   get: (sessionId: string) => Promise<DomainSession>
   stop: (sessionId: string) => Promise<void>
   start: (sessionId: string) => Promise<DomainSession>
+  delete: (sessionId: string) => Promise<void>
 }
diff --git a/components/ambient-ui/src/queries/index.ts b/components/ambient-ui/src/queries/index.ts
index e52c4ef63..0d90ea058 100644
--- a/components/ambient-ui/src/queries/index.ts
+++ b/components/ambient-ui/src/queries/index.ts
@@ -1,5 +1,6 @@
 export { queryKeys } from './query-keys'
-export { useSessions, useSession, useStopSession, useStartSession } from './use-sessions'
+export { useSessions, useSession, useStopSession, useStartSession, useDeleteSession } from './use-sessions'
 export { useProjects, useProject } from './use-projects'
 export { useSendFeedback } from './use-send-feedback'
 export { useSessionMessages } from './use-session-messages'
+export { useSendMessage } from './use-send-message'
diff --git a/components/ambient-ui/src/queries/use-send-message.ts b/components/ambient-ui/src/queries/use-send-message.ts
new file mode 100644
index 000000000..7122707c8
--- /dev/null
+++ b/components/ambient-ui/src/queries/use-send-message.ts
@@ -0,0 +1,30 @@
+'use client'
+
+import { useRef } from 'react'
+import { useMutation, useQueryClient } from '@tanstack/react-query'
+import type { SessionMessagesPort } from '@/ports/session-messages'
+import { createSessionMessagesAdapterWithFetch } from '@/adapters/session-messages'
+import { queryKeys } from './query-keys'
+
+export function useSendMessage(sessionId: string, port?: SessionMessagesPort) {
+  const defaultPortRef = useRef<SessionMessagesPort | null>(null)
+  if (!defaultPortRef.current && !port) {
+    defaultPortRef.current = createSessionMessagesAdapterWithFetch()
+  }
+  const adapter = port ?? defaultPortRef.current!
+  const queryClient = useQueryClient()
+
+  return useMutation({
+    mutationFn: async (payload: string) => {
+      return adapter.send(sessionId, {
+        eventType: 'user',
+        payload,
+      })
+    },
+    onSuccess: () => {
+      void queryClient.invalidateQueries({
+        queryKey: queryKeys.messages.list(sessionId),
+      })
+    },
+  })
+}
diff --git a/components/ambient-ui/src/queries/use-sessions.ts b/components/ambient-ui/src/queries/use-sessions.ts
index 6c3725227..baf1e205f 100644
--- a/components/ambient-ui/src/queries/use-sessions.ts
+++ b/components/ambient-ui/src/queries/use-sessions.ts
@@ -113,3 +113,15 @@ export function useStartSession(port?: SessionsPort) {
     },
   })
 }
+
+export function useDeleteSession(port?: SessionsPort) {
+  const queryClient = useQueryClient()
+  const adapter = port ?? getDefaultPort()
+
+  return useMutation({
+    mutationFn: (sessionId: string) => adapter.delete(sessionId),
+    onSuccess: () => {
+      queryClient.invalidateQueries({ queryKey: queryKeys.sessions.all })
+    },
+  })
+}
diff --git a/components/runners/ambient-runner/ambient_runner/bridges/claude/operational_events.py b/components/runners/ambient-runner/ambient_runner/bridges/claude/operational_events.py
index 570342271..78b26729f 100644
--- a/components/runners/ambient-runner/ambient_runner/bridges/claude/operational_events.py
+++ b/components/runners/ambient-runner/ambient_runner/bridges/claude/operational_events.py
@@ -24,22 +24,23 @@
 # ag_ui.core.EventType.TOOL_CALL_RESULT is emitted by handlers.py:199
 # (ToolCallResultEvent after ToolCallEndEvent). See test_operational_events.py.
 _AGUI_TO_EVENT_TYPE = {
-    "TOOL_CALL_START": "tool_use",
+    "TOOL_CALL_END": "tool_use",
     "TOOL_CALL_RESULT": "tool_result",
     "RUN_STARTED": "lifecycle",
     "RUN_FINISHED": "lifecycle",
     "RUN_ERROR": "error",
 }
 
-_SKIP_TYPES = frozenset({
-    "TOOL_CALL_ARGS",
-    "TOOL_CALL_END",
-    "TEXT_MESSAGE_START",
-    "TEXT_MESSAGE_CONTENT",
-    "TEXT_MESSAGE_END",
-    "STATE_SNAPSHOT",
-    "MESSAGES_SNAPSHOT",
-})
+# TOOL_CALL_START and TOOL_CALL_ARGS are handled by explicit early returns in consume().
+_SKIP_TYPES = frozenset(
+    {
+        "TEXT_MESSAGE_START",
+        "TEXT_MESSAGE_CONTENT",
+        "TEXT_MESSAGE_END",
+        "STATE_SNAPSHOT",
+        "MESSAGES_SNAPSHOT",
+    }
+)
 
 
 def _event_type_str(event: BaseEvent) -> Optional[str]:
@@ -49,11 +50,26 @@ def _event_type_str(event: BaseEvent) -> Optional[str]:
     return raw.value if hasattr(raw, "value") else str(raw)
 
 
-def _build_payload(event_type_str: str, event: BaseEvent) -> str:
-    if event_type_str == "TOOL_CALL_START":
-        name = getattr(event, "tool_call_name", None) or "unknown"
+def _build_payload(
+    event_type_str: str,
+    event: BaseEvent,
+    pending_tools: Optional[dict] = None,
+) -> str:
+    if event_type_str == "TOOL_CALL_END":
         tool_id = getattr(event, "tool_call_id", None) or ""
-        return json.dumps({"tool": name, "tool_call_id": tool_id})
+        info = (pending_tools or {}).get(tool_id, {})
+        name = info.get("name", "unknown")
+        args = info.get("args", "")
+        payload: dict = {"tool": name, "tool_call_id": tool_id}
+        if args:
+            try:
+                parsed = json.loads(args)
+                payload["input"] = (
+                    parsed if isinstance(parsed, dict) else {"value": parsed}
+                )
+            except (json.JSONDecodeError, TypeError):
+                payload["input"] = {"raw": args}
+        return json.dumps(payload)
 
     if event_type_str == "TOOL_CALL_RESULT":
         tool_id = getattr(event, "tool_call_id", None) or ""
@@ -79,7 +95,9 @@ def _build_payload(event_type_str: str, event: BaseEvent) -> str:
         payload = {"custom_event": name}
         if value is not None:
             try:
-                payload["value"] = json.loads(value) if isinstance(value, str) else value
+                payload["value"] = (
+                    json.loads(value) if isinstance(value, str) else value
+                )
             except (json.JSONDecodeError, TypeError):
                 payload["value"] = str(value)
         return json.dumps(payload)
@@ -97,12 +115,27 @@ def __init__(
     ) -> None:
         self._session_id = session_id
         self._grpc_client = grpc_client
+        self._pending_tools: dict[str, dict[str, str]] = {}
 
     async def consume(self, event: BaseEvent) -> None:
         event_type_str = _event_type_str(event)
         if event_type_str is None:
             return
 
+        # Accumulate tool call info for TOOL_CALL_END
+        if event_type_str == "TOOL_CALL_START":
+            tool_id = getattr(event, "tool_call_id", None) or ""
+            name = getattr(event, "tool_call_name", None) or "unknown"
+            self._pending_tools[tool_id] = {"name": name, "args": ""}
+            return
+
+        if event_type_str == "TOOL_CALL_ARGS":
+            tool_id = getattr(event, "tool_call_id", None) or ""
+            delta = getattr(event, "delta", None) or ""
+            if tool_id in self._pending_tools:
+                self._pending_tools[tool_id]["args"] += delta
+            return
+
         if event_type_str in _SKIP_TYPES:
             return
 
@@ -121,7 +154,10 @@ async def consume(self, event: BaseEvent) -> None:
         if self._grpc_client is None:
             return
 
-        payload = _build_payload(event_type_str, event)
+        payload = _build_payload(event_type_str, event, self._pending_tools)
+        if event_type_str == "TOOL_CALL_END":
+            tool_id = getattr(event, "tool_call_id", None) or ""
+            self._pending_tools.pop(tool_id, None)
         client = self._grpc_client
         session_id = self._session_id
 
diff --git a/components/runners/ambient-runner/tests/test_operational_events.py b/components/runners/ambient-runner/tests/test_operational_events.py
index 4a5f9541b..67e803f6a 100644
--- a/components/runners/ambient-runner/tests/test_operational_events.py
+++ b/components/runners/ambient-runner/tests/test_operational_events.py
@@ -37,6 +37,7 @@ class FakeEvent:
     code: str = ""
     name: str = ""
     value: Optional[str] = None
+    delta: str = ""
 
 
 @dataclass
@@ -68,15 +69,20 @@ def test_none_type(self):
 
 
 class TestBuildPayload:
-    def test_tool_call_start(self):
-        event = FakeEvent(
-            type=FakeEventType.TOOL_CALL_START,
-            tool_call_name="Read",
-            tool_call_id="tc-123",
-        )
-        payload = json.loads(_build_payload("TOOL_CALL_START", event))
+    def test_tool_call_end_with_accumulated_args(self):
+        event = FakeEvent(type=FakeEventType.TOOL_CALL_END, tool_call_id="tc-123")
+        pending = {"tc-123": {"name": "Read", "args": '{"file_path": "/app/main.py"}'}}
+        payload = json.loads(_build_payload("TOOL_CALL_END", event, pending))
         assert payload["tool"] == "Read"
         assert payload["tool_call_id"] == "tc-123"
+        assert payload["input"] == {"file_path": "/app/main.py"}
+
+    def test_tool_call_end_without_args(self):
+        event = FakeEvent(type=FakeEventType.TOOL_CALL_END, tool_call_id="tc-456")
+        pending = {"tc-456": {"name": "Bash", "args": ""}}
+        payload = json.loads(_build_payload("TOOL_CALL_END", event, pending))
+        assert payload["tool"] == "Bash"
+        assert "input" not in payload
 
     def test_tool_call_result(self):
         event = FakeEvent(
@@ -151,17 +157,41 @@ def writer(self, grpc_client):
             grpc_client=grpc_client,
         )
 
-    def test_tool_call_start_pushes_tool_use(self, writer, grpc_client):
+    def test_tool_call_start_accumulates_no_push(self, writer, grpc_client):
         event = FakeEvent(
             type=FakeEventType.TOOL_CALL_START,
             tool_call_name="Bash",
             tool_call_id="tc-1",
         )
         asyncio.get_event_loop().run_until_complete(writer.consume(event))
+        assert len(grpc_client.session_messages.calls) == 0
+
+    def test_full_tool_call_flow_pushes_with_args(self, writer, grpc_client):
+        start = FakeEvent(
+            type=FakeEventType.TOOL_CALL_START,
+            tool_call_name="Read",
+            tool_call_id="tc-1",
+        )
+        args = FakeEvent(
+            type=FakeEventType.TOOL_CALL_ARGS,
+            tool_call_id="tc-1",
+            delta='{"file_path": "/app/main.py"}',
+        )
+        end = FakeEvent(
+            type=FakeEventType.TOOL_CALL_END,
+            tool_call_id="tc-1",
+        )
+        loop = asyncio.get_event_loop()
+        loop.run_until_complete(writer.consume(start))
+        loop.run_until_complete(writer.consume(args))
+        loop.run_until_complete(writer.consume(end))
         assert len(grpc_client.session_messages.calls) == 1
         call = grpc_client.session_messages.calls[0]
         assert call["session_id"] == "sess-001"
         assert call["event_type"] == "tool_use"
+        payload = json.loads(call["payload"])
+        assert payload["tool"] == "Read"
+        assert payload["input"] == {"file_path": "/app/main.py"}
 
     def test_tool_call_result_pushes_tool_result(self, writer, grpc_client):
         event = FakeEvent(
@@ -208,8 +238,10 @@ def test_text_message_content_skipped(self, writer, grpc_client):
         asyncio.get_event_loop().run_until_complete(writer.consume(event))
         assert len(grpc_client.session_messages.calls) == 0
 
-    def test_tool_call_args_skipped(self, writer, grpc_client):
-        event = FakeEvent(type=FakeEventType.TOOL_CALL_ARGS)
+    def test_tool_call_args_accumulates_no_push(self, writer, grpc_client):
+        event = FakeEvent(
+            type=FakeEventType.TOOL_CALL_ARGS, tool_call_id="tc-orphan", delta="data"
+        )
         asyncio.get_event_loop().run_until_complete(writer.consume(event))
         assert len(grpc_client.session_messages.calls) == 0
 
diff --git a/specs/ambient-ui/ambient-ui.spec.md b/specs/ambient-ui/ambient-ui.spec.md
index 9e2a41b52..a691d0811 100644
--- a/specs/ambient-ui/ambient-ui.spec.md
+++ b/specs/ambient-ui/ambient-ui.spec.md
@@ -318,10 +318,65 @@ Condition colors SHALL reflect semantic health, not literal True/False values. "
 
 - GIVEN a Running session
 - WHEN the Chat tab renders
-- THEN it displays a full AG-UI chat interface with streaming messages
-- AND user messages, agent responses, tool calls (with name, arguments, duration, success/fail), and reasoning blocks are rendered
-- AND the user can send messages via an input field
-- AND the agent's current status is displayed near the input
+- THEN it displays a full AG-UI chat interface with messages
+- AND user messages are styled distinctly from assistant messages
+- AND assistant messages render as Markdown (headings, lists, code blocks, tables, links)
+- AND tool calls render as collapsible blocks showing tool name, arguments (when available), and result
+- AND the user can send messages via an input field (Enter to send, Shift+Enter for newline)
+- AND the agent's current status is displayed as a phase badge near the input
+- AND the input is disabled when the session is not in Running phase
+
+Note: the runner currently persists one `assistant` message per turn (final text only). Intermediate assistant text and individual tool call arguments are not yet persisted as separate messages — they arrive via the operational event writer with tool name and result only. Full streaming with intermediate text requires the SSE-Driven Updates requirement.
+
+### Requirement: Persistent Chat Sidebar
+
+The Ambient UI SHALL support popping a session's chat into a persistent sidebar panel that remains visible across page navigation. The sidebar allows the user to monitor and interact with an agent while performing other tasks in the UI.
+
+Any view that displays a session (fleet table row, session detail header, chat tab) SHALL offer a control to open the chat sidebar for that session. Only one chat sidebar MAY be open at a time; opening a different session's chat SHALL replace the current one.
+
+#### Scenario: Open chat sidebar from Chat tab
+
+- GIVEN the user is viewing a session's Chat tab
+- WHEN the user clicks the "Pop out" button
+- THEN the chat panel moves from the tab content area into a right-edge sidebar
+- AND the Chat tab displays a message indicating the chat is open in the sidebar
+- AND the sidebar shows the session name and phase badge
+
+#### Scenario: Open chat sidebar from fleet table
+
+- GIVEN the user is viewing the fleet table
+- WHEN the user clicks the chat icon on a session row
+- THEN the chat sidebar opens for that session
+- AND the fleet table remains visible alongside the sidebar
+
+#### Scenario: Sidebar persists across navigation
+
+- GIVEN the chat sidebar is open for session A
+- WHEN the user navigates to a different page (fleet list, another session, settings)
+- THEN the sidebar remains open and continues displaying session A's chat
+- AND new messages continue to appear via polling or SSE
+
+#### Scenario: Replace sidebar session
+
+- GIVEN the chat sidebar is open for session A
+- WHEN the user opens the chat sidebar for session B
+- THEN the sidebar switches to session B's chat
+- AND session A's chat is no longer displayed
+
+#### Scenario: Close sidebar
+
+- GIVEN the chat sidebar is open
+- WHEN the user clicks the close button on the sidebar
+- THEN the sidebar dismisses
+- AND if the user navigates back to the session's Chat tab, it renders inline again
+
+#### Scenario: Sidebar layout
+
+- GIVEN the chat sidebar is open
+- THEN it docks to the right edge of the viewport
+- AND it is resizable by dragging the left edge
+- AND it is collapsible to a narrow strip showing the session name
+- AND the main content area shrinks to accommodate the sidebar
 
 ### Requirement: Timestamp Toggle
 
@@ -839,4 +894,5 @@ This section documents API endpoints and capabilities that this spec depends on
 | Tool metrics computed client-side | The API stores raw SessionMessages. Aggregating tool call stats is a UI concern, not an API concern. |
 | SSE for sessions, polling for rest | Sessions have real-time SSE streams. Credentials, schedules, and agents change infrequently — polling is sufficient and simpler. |
 | Single interaction pattern per entity | Agent rows: sidebar only (no expand + sidebar). Fleet rows: detail view only. Reduces cognitive load per Krug's "Don't Make Me Think." |
+| Chat sidebar is app-level, not tab-level | The sidebar lives in the root layout, not the session detail page. This enables cross-page persistence. State is managed via React context at the dashboard layout level. |
 | Feedback delivery is context-dependent | Running session → session message (immediate). Stopped session → agent inbox (queued). Matches the platform's existing message model. |