diff --git a/apps/server/src/environment/ServerEnvironment.test.ts b/apps/server/src/environment/ServerEnvironment.test.ts
index 7cebccb2a1f7c..4d631dbc61889 100644
--- a/apps/server/src/environment/ServerEnvironment.test.ts
+++ b/apps/server/src/environment/ServerEnvironment.test.ts
@@ -77,7 +77,8 @@ it.layer(NodeServices.layer)("ServerEnvironmentLive", (it) => {
   it.effect("publishes proven install ownership only for manually updated servers", () =>
     Effect.gen(function* () {
       const fs = yield* FileSystem.FileSystem;
-      const baseDir = yield* fs.makeTempDirectoryScoped();
+      const platform = yield* HostProcess.Platform;
+      const baseDir = yield* fs.realPath(yield* fs.makeTempDirectoryScoped());
       const prefix = `${baseDir}/node`;
       const entry = `${prefix}/lib/node_modules/t3/dist/bin.mjs`;
       yield* fs.makeDirectory(`${prefix}/lib/node_modules/t3/dist`, { recursive: true });
@@ -103,11 +104,10 @@ it.layer(NodeServices.layer)("ServerEnvironmentLive", (it) => {
           ),
           Effect.provideService(HostProcess.Arguments, ["node", entry]),
           Effect.provideService(HostProcess.IsExecutable, false),
-          Effect.provideService(HostProcess.Platform, "linux"),
           Effect.provideService(HostProcess.Environment, {}),
         );
         expect(descriptor.capabilities.serverInstallation).toEqual(
-          mode === "web" ? { kind: "npm-global", prefix } : undefined,
+          mode === "web" && platform !== "win32" ? { kind: "npm-global", prefix } : undefined,
         );
         expect(descriptor.capabilities.serverSelfUpdate).toBe(
           mode === "web" ? undefined : "desktop-managed",
diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
index 8494c4cab7812..555849d91ff8b 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
@@ -1720,6 +1720,11 @@ describe("ClaudeAdapterV2 resume compaction", () => {
 });
 
 describe("ClaudeAdapterV2 attachments", () => {
+  const messageText = (content: SDKUserMessage["message"]["content"]) =>
+    typeof content === "string"
+      ? content
+      : content.flatMap((block) => (block.type === "text" ? [block.text] : [])).join("\n");
+
   it.effect.each([
     ...[
       "retained-images",
@@ -1972,7 +1977,7 @@ describe("ClaudeAdapterV2 attachments", () => {
             yield* deliver;
             const retried = offeredMessages.at(-1)!.message.content;
             assert.notInclude(JSON.stringify(retried), '"type":"document"');
-            assert.include(JSON.stringify(retried), documentPath);
+            assert.include(messageText(retried), documentPath);
             assert.isBelow(Buffer.byteLength(JSON.stringify(offeredMessages)), 32_000_000);
             return;
           }
@@ -2021,7 +2026,7 @@ describe("ClaudeAdapterV2 attachments", () => {
                 typeof sent === "string" ? [] : sent.filter((block) => block.type === "image"),
                 budget === "partial-images" ? 1 : 0,
               );
-              assert.include(JSON.stringify(sent), imagePath);
+              assert.include(messageText(sent), imagePath);
               yield* runtime.steerTurn({
                 threadId,
                 runId: RunId.make("run-claude-attachments"),
@@ -2040,7 +2045,7 @@ describe("ClaudeAdapterV2 attachments", () => {
                   : steered.filter((block) => block.type === "image"),
                 0,
               );
-              assert.include(JSON.stringify(steered), imagePath);
+              assert.include(messageText(steered), imagePath);
               assert.isBelow(
                 Buffer.byteLength(
                   JSON.stringify(offeredMessages.map((message) => message.message)),
@@ -2102,7 +2107,7 @@ describe("ClaudeAdapterV2 attachments", () => {
               0,
               budget,
             );
-            assert.include(JSON.stringify(sent), documentPath);
+            assert.include(messageText(sent), documentPath);
             return;
           }
           if (!resumed) {
@@ -2315,7 +2320,7 @@ describe("ClaudeAdapterV2 attachments", () => {
             );
             if (scenario === "text-only")
               assert.equal(sent, ultrathink ? "Ultrathink:\nContinue." : "Continue.");
-            else assert.include(JSON.stringify(sent), documentPath);
+            else assert.include(messageText(sent), documentPath);
           }
         }).pipe(
           Effect.provide(
@@ -4271,6 +4276,7 @@ describe("ClaudeAdapterV2 background wake turns", () => {
           "true",
         );
       }).pipe(
+        Effect.provideService(HostProcess.Platform, "linux"),
         Effect.provide(
           Layer.mergeAll(IdAllocator.layer, McpProviderSessions.layer, NodeServices.layer),
         ),