diff --git a/docker/run/fs/exe/self_update_manager.py b/docker/run/fs/exe/self_update_manager.py
index d963541c2..d3abaf266 100644
--- a/docker/run/fs/exe/self_update_manager.py
+++ b/docker/run/fs/exe/self_update_manager.py
@@ -1055,6 +1055,23 @@ def queue_update_request(
     return payload
 
 
+def installed_target_matches_request(
+    current_info: dict[str, str],
+    *,
+    requested_branch: str,
+    requested_tag: str,
+) -> bool:
+    normalized_tag = requested_tag.strip()
+    if not normalized_tag or is_latest_selector_tag(normalized_tag):
+        return False
+
+    current_branch = current_info.get("branch", "").strip()
+    if requested_branch.strip() and current_branch != requested_branch.strip():
+        return False
+
+    return current_info.get("describe", "").strip() == normalized_tag
+
+
 def trigger_update_command(args: list[str]) -> int:
     parser = argparse.ArgumentParser(
         prog="trigger_self_update.sh",
@@ -1137,11 +1154,10 @@ def docker_run_ui() -> int:
             current = get_repo_version_info(REPO_DIR)
             requested_branch = str(request_data.get("branch", "")).strip()
             requested_tag = str(request_data.get("tag", "")).strip()
-            current_branch = current.get("branch", "").strip()
-            if (
-                requested_tag
-                and current["short_tag"] == requested_tag
-                and (not requested_branch or current_branch == requested_branch)
+            if installed_target_matches_request(
+                current,
+                requested_branch=requested_branch,
+                requested_tag=requested_tag,
             ):
                 logger.log(
                     "Requested tag already matches the installed version, skipping file replacement."
diff --git a/tests/test_self_update_tag_filter.py b/tests/test_self_update_tag_filter.py
index d6298e477..dbbb70d48 100644
--- a/tests/test_self_update_tag_filter.py
+++ b/tests/test_self_update_tag_filter.py
@@ -393,7 +393,9 @@ def test_self_update_frontend_uses_preloaded_select():
     assert "getLastStatusBadgeClass(status)" in content
     assert "this.info?.current?.display_version" in content
     assert "resetRestartState()" in content
-    assert "restartRequestError" in content
+    assert "restartRequestStarted" in content
+    assert "restartResponse.status >= 500" in content
+    assert "while Agent Zero was shutting down" in content
     assert "await notificationStore.frontendWarning(" not in content
     assert "status-pill-error" in content
     assert "status-pill-success" in content
@@ -658,6 +660,47 @@ def test_self_update_manager_explicit_tag_uses_peeled_commit(monkeypatch):
     assert resolved["expected_commit"] == "192d6e2cae1a85c0a2e7a6ecf41c153b39f1b4c6"
 
 
+def test_self_update_manager_skip_check_requires_exact_describe_match():
+    manager = load_self_update_manager()
+
+    assert (
+        manager.installed_target_matches_request(
+            {
+                "branch": "development",
+                "describe": "v1.11",
+                "short_tag": "v1.11",
+            },
+            requested_branch="development",
+            requested_tag="v1.11",
+        )
+        is True
+    )
+    assert (
+        manager.installed_target_matches_request(
+            {
+                "branch": "development",
+                "describe": "v1.11-12-ge9d9c93d",
+                "short_tag": "v1.11",
+            },
+            requested_branch="development",
+            requested_tag="v1.11",
+        )
+        is False
+    )
+    assert (
+        manager.installed_target_matches_request(
+            {
+                "branch": "development",
+                "describe": "v1.11",
+                "short_tag": "v1.11",
+            },
+            requested_branch="development",
+            requested_tag="latest",
+        )
+        is False
+    )
+
+
 def test_self_update_manager_fetch_release_refs_checks_peeled_tag_commit(monkeypatch):
     manager = load_self_update_manager()
     commands = []
diff --git a/webui/components/settings/external/self-update-store.js b/webui/components/settings/external/self-update-store.js
index 515e4b33b..87cf02b14 100644
--- a/webui/components/settings/external/self-update-store.js
+++ b/webui/components/settings/external/self-update-store.js
@@ -497,9 +497,10 @@ const model = {
     );
     this.ensureProgressOverlay();
 
-    let restartRequestError = null;
+    let restartRequestStarted = false;
     try {
       const token = await API.getCsrfToken();
+      restartRequestStarted = true;
       const restartResponse = await fetch("/api/restart", {
         method: "POST",
         credentials: "same-origin",
@@ -511,19 +512,36 @@ const model = {
         body: JSON.stringify({}),
       });
       if (restartResponse && !restartResponse.ok) {
-        restartRequestError = new Error(
-          `Restart request failed with HTTP ${restartResponse.status}.`
+        if (restartResponse.status >= 500) {
+          console.warn(
+            `Restart request returned HTTP ${restartResponse.status} while Agent Zero was shutting down. Continuing to wait for the new runtime.`
+          );
+          this.setRestartState(
+            "Restarting backend",
+            "Agent Zero is shutting down and applying the update. Waiting for the new runtime to come back healthy."
+          );
+        } else {
+          throw new Error(
+            `Restart request failed with HTTP ${restartResponse.status}.`
+          );
+        }
+      } else {
+        this.setRestartState(
+          "Restarting backend",
+          "Agent Zero accepted the restart request. Waiting for the updater to take over."
         );
-        throw restartRequestError;
       }
     } catch (error) {
-      if (restartRequestError && error === restartRequestError) {
+      if (!restartRequestStarted) {
         this.restarting = false;
         this.resetRestartState();
         this.removeProgressOverlay();
         throw error;
       }
-      // The restart request often terminates the backend mid-flight.
+      console.warn(
+        "Restart request connection closed while Agent Zero was restarting:",
+        error
+      );
     }
 
     const maxWaitMs =