diff --git a/.changeset/init-removal-prompt-keeps-skill.md b/.changeset/init-removal-prompt-keeps-skill.md
new file mode 100644
index 00000000..94f97471
--- /dev/null
+++ b/.changeset/init-removal-prompt-keeps-skill.md
@@ -0,0 +1,5 @@
+---
+"@taskless/cli": patch
+---
+
+`init` no longer asks to "Remove Taskless from .claude/" when an upgrade only retires a stub there. A directory that keeps its Taskless skill is now described as losing that stub ("Remove 1 stub from .claude/?"). "Remove Taskless from" is reserved for a directory you deselected.
diff --git a/packages/cli/src/wizard/steps/summary.ts b/packages/cli/src/wizard/steps/summary.ts
index 82a2e62d..b546e008 100644
--- a/packages/cli/src/wizard/steps/summary.ts
+++ b/packages/cli/src/wizard/steps/summary.ts
@@ -172,26 +172,46 @@ function describeProjectEdits(
  * misleading; when only canonical removals are present the message falls back
  * to a generic prompt. Only meaningful when {@link InstallDiff.hasRemovals}
  * is true.
+ *
+ * "Remove Taskless from" is said only of a target that keeps nothing. A target
+ * that loses a retired stub but keeps its skill is still a Taskless install,
+ * and telling someone it is being uninstalled makes them decline an upgrade
+ * that removes one command file.
  */
 export function buildRemovalConfirmMessage(
   diff: InstallDiff,
   options: { editsSettings?: boolean } = {}
 ): string {
-  const clauses: string[] = [];
+  const uninstalled: string[] = [];
+  const trimmed: string[] = [];
   for (const entry of diff.entries) {
     if (entry.mode === "canonical") continue;
     const count = entry.removals.skills.length + entry.removals.commands.length;
     if (count === 0) continue;
-    clauses.push(
-      `${entry.target}/ (${String(count)} stub${count === 1 ? "" : "s"})`
-    );
+    const stubs = `${String(count)} stub${count === 1 ? "" : "s"}`;
+    const kept =
+      entry.additions.skills.length +
+      entry.additions.commands.length +
+      entry.unchanged.skills.length +
+      entry.unchanged.commands.length;
+    if (kept === 0) {
+      uninstalled.push(`${entry.target}/ (${stubs})`);
+    } else {
+      trimmed.push(`${stubs} from ${entry.target}/`);
+    }
   }
-  if (clauses.length === 0) {
+  if (uninstalled.length === 0 && trimmed.length === 0) {
     return options.editsSettings === true
       ? "Some files recorded in the previous install will be removed. Proceed, and make these changes to your settings?"
       : "Some files recorded in the previous install will be removed. Proceed?";
   }
+  const clauses = [
+    ...(uninstalled.length > 0
+      ? [`Taskless from ${uninstalled.join(", ")}`]
+      : []),
+    ...trimmed,
+  ];
   return options.editsSettings === true
-    ? `Remove Taskless from ${clauses.join(", ")}, and make these changes to your settings?`
-    : `Remove Taskless from ${clauses.join(", ")}?`;
+    ? `Remove ${clauses.join(", ")}, and make these changes to your settings?`
+    : `Remove ${clauses.join(", ")}?`;
 }
diff --git a/packages/cli/test/wizard-steps.test.ts b/packages/cli/test/wizard-steps.test.ts
index 15851127..c750dc11 100644
--- a/packages/cli/test/wizard-steps.test.ts
+++ b/packages/cli/test/wizard-steps.test.ts
@@ -218,14 +218,15 @@ function diffEntry(
   target: string,
   removedSkills: string[],
   removedCommands: string[] = [],
-  mode: "reference" | "canonical" = "reference"
+  mode: "reference" | "canonical" = "reference",
+  unchangedSkills: string[] = []
 ) {
   return {
     target,
     mode,
     additions: { skills: [], commands: [] },
     removals: { skills: removedSkills, commands: removedCommands },
-    unchanged: { skills: [], commands: [] },
+    unchanged: { skills: unchangedSkills, commands: [] },
   };
 }
 
@@ -246,6 +247,44 @@ describe("buildRemovalConfirmMessage", () => {
     );
   });
 
+  it("does not call a target that keeps its skill an uninstall", async () => {
+    // An upgrade that retires the /tskl command leaves the skill in place, so
+    // the question is about one stub, not about Taskless leaving .claude/.
+    const { buildRemovalConfirmMessage } =
+      await import("../src/wizard/steps/summary");
+    const message = buildRemovalConfirmMessage(
+      {
+        entries: [
+          diffEntry(".taskless", [], ["tskl.md"], "canonical", ["taskless"]),
+          diffEntry(".claude", [], ["tskl.md"], "reference", ["taskless"]),
+        ],
+        hasAdditions: false,
+        hasRemovals: true,
+      },
+      { editsSettings: true }
+    );
+    expect(message).toBe(
+      "Remove 1 stub from .claude/, and make these changes to your settings?"
+    );
+    expect(message).not.toContain("Remove Taskless");
+  });
+
+  it("names uninstalled targets before trimmed ones", async () => {
+    const { buildRemovalConfirmMessage } =
+      await import("../src/wizard/steps/summary");
+    const message = buildRemovalConfirmMessage({
+      entries: [
+        diffEntry(".claude", [], ["tskl.md"], "reference", ["taskless"]),
+        diffEntry(".cursor", ["taskless"], ["tskl.md"]),
+      ],
+      hasAdditions: false,
+      hasRemovals: true,
+    });
+    expect(message).toBe(
+      "Remove Taskless from .cursor/ (2 stubs), 1 stub from .claude/?"
+    );
+  });
+
   it("folds the settings changes into the same question", async () => {
     const { buildRemovalConfirmMessage } =
       await import("../src/wizard/steps/summary");