diff --git a/apps/server/src/vcs/GitVcsDriverCore.test.ts b/apps/server/src/vcs/GitVcsDriverCore.test.ts
index c0621f2c99d7..3c7f351bcc32 100644
--- a/apps/server/src/vcs/GitVcsDriverCore.test.ts
+++ b/apps/server/src/vcs/GitVcsDriverCore.test.ts
@@ -1345,6 +1345,77 @@ it.layer(TestLayer)("GitVcsDriver core integration", (it) => {
         assert.equal(result.branch, current);
       }),
     );
+
+    it.effect("explains checkout failures caused by uncommitted changes", () =>
+      Effect.gen(function* () {
+        const cwd = yield* makeTmpDir();
+        const { initialBranch } = yield* initRepoWithCommit(cwd);
+        const driver = yield* GitVcsDriver.GitVcsDriver;
+
+        yield* git(cwd, ["checkout", "-b", "feature/target"]);
+        yield* writeTextFile(cwd, "README.md", "# target\n");
+        yield* git(cwd, ["add", "."]);
+        yield* git(cwd, ["commit", "-m", "target commit"]);
+        yield* git(cwd, ["checkout", initialBranch]);
+        yield* writeTextFile(cwd, "README.md", "# dirty\n");
+
+        const error = yield* driver.switchRef({ cwd, refName: "feature/target" }).pipe(Effect.flip);
+
+        assert.deepInclude(error, {
+          _tag: "GitCommandError",
+          operation: "GitVcsDriver.switchRef.checkout",
+          cwd,
+        });
+        assert.include(error.detail, "uncommitted changes would be overwritten");
+        assert.include(error.detail, "Commit, stash, or discard");
+        assert.notProperty(error, "stderr");
+      }),
+    );
+
+    it.effect("explains checkout failures when the branch is checked out in another worktree", () =>
+      Effect.gen(function* () {
+        const cwd = yield* makeTmpDir();
+        yield* initRepoWithCommit(cwd);
+        const worktreesRoot = yield* makeTmpDir("git-vcs-driver-worktrees-");
+        const fileSystem = yield* FileSystem.FileSystem;
+        const pathService = yield* Path.Path;
+        const worktreePath = pathService.join(worktreesRoot, "linked-worktree");
+        yield* fileSystem.makeDirectory(worktreesRoot, { recursive: true });
+        const driver = yield* GitVcsDriver.GitVcsDriver;
+
+        yield* git(cwd, ["worktree", "add", "-b", "feature/linked", worktreePath]);
+
+        const error = yield* driver.switchRef({ cwd, refName: "feature/linked" }).pipe(Effect.flip);
+
+        assert.deepInclude(error, {
+          _tag: "GitCommandError",
+          operation: "GitVcsDriver.switchRef.checkout",
+          cwd,
+        });
+        assert.include(error.detail, "already checked out in another worktree");
+        assert.notProperty(error, "stderr");
+      }),
+    );
+
+    it.effect("explains checkout failures for unknown refs", () =>
+      Effect.gen(function* () {
+        const cwd = yield* makeTmpDir();
+        yield* initRepoWithCommit(cwd);
+        const driver = yield* GitVcsDriver.GitVcsDriver;
+
+        const error = yield* driver
+          .switchRef({ cwd, refName: "does/not-exist-xyz" })
+          .pipe(Effect.flip);
+
+        assert.deepInclude(error, {
+          _tag: "GitCommandError",
+          operation: "GitVcsDriver.switchRef.checkout",
+          cwd,
+        });
+        assert.include(error.detail, "not found locally or on remotes");
+        assert.notProperty(error, "stderr");
+      }),
+    );
   });
 
   describe("worktree operations", () => {
diff --git a/apps/server/src/vcs/GitVcsDriverCore.ts b/apps/server/src/vcs/GitVcsDriverCore.ts
index f1fb1b7a7b18..552961786b3e 100644
--- a/apps/server/src/vcs/GitVcsDriverCore.ts
+++ b/apps/server/src/vcs/GitVcsDriverCore.ts
@@ -443,6 +443,27 @@ function isMissingWorktreeStderr(stderr: string): boolean {
   );
 }
 
+// Classifies `git checkout` stderr into a closed set of static sentences.
+// Raw stderr never leaves the driver (it can carry remote URLs with embedded
+// credentials), so every branch returns a fixed string that names the cause
+// and the fix instead of echoing git's output.
+function classifySwitchRefCheckoutError(stderr: string): string {
+  const normalized = stderr.toLowerCase();
+  if (normalized.includes("used by worktree")) {
+    return "git checkout failed because the branch is already checked out in another worktree. Switch in that worktree or check out a different branch.";
+  }
+  if (
+    normalized.includes("would be overwritten by checkout") ||
+    normalized.includes("stash them before you switch")
+  ) {
+    return "git checkout failed because uncommitted changes would be overwritten. Commit, stash, or discard those changes, then try again.";
+  }
+  if (normalized.includes("did not match any file") || normalized.includes("pathspec")) {
+    return "git checkout failed because the ref was not found locally or on remotes. Fetch the latest refs and check the branch name, then try again.";
+  }
+  return "git checkout failed";
+}
+
 interface Trace2Monitor {
   readonly env: NodeJS.ProcessEnv;
   readonly flush: Effect.Effect<void, never>;
@@ -3207,10 +3228,33 @@ export const makeGitVcsDriverCore = Effect.fn("makeGitVcsDriverCore")(function*
               ? ["checkout", localTrackingBranch]
               : ["checkout", input.refName];
 
-      yield* executeGit("GitVcsDriver.switchRef.checkout", input.cwd, checkoutArgs, {
-        timeoutMs: 10_000,
-        fallbackErrorDetail: "git checkout failed",
-      });
+      const checkoutResult = yield* executeGit(
+        "GitVcsDriver.switchRef.checkout",
+        input.cwd,
+        checkoutArgs,
+        {
+          timeoutMs: 10_000,
+          allowNonZeroExit: true,
+        },
+      );
+      if (checkoutResult.exitCode !== 0) {
+        // Raw stderr stays out of the wire error (it can carry secrets); the
+        // classified detail names the cause and the fix instead.
+        yield* Effect.logWarning(
+          `GitVcsDriver.switchRef: git checkout exited with code ${checkoutResult.exitCode} (stderr length ${checkoutResult.stderr.length}).`,
+        );
+        return yield* new GitCommandError({
+          ...gitCommandContext({
+            operation: "GitVcsDriver.switchRef.checkout",
+            cwd: input.cwd,
+            args: checkoutArgs,
+          }),
+          detail: classifySwitchRefCheckoutError(checkoutResult.stderr),
+          ...(checkoutResult.exitCode === null ? {} : { exitCode: checkoutResult.exitCode }),
+          stdoutLength: checkoutResult.stdout.length,
+          stderrLength: checkoutResult.stderr.length,
+        });
+      }
 
       const refName = yield* runGitStdout("GitVcsDriver.switchRef.currentBranch", input.cwd, [
         "branch",