diff --git a/apps/web/src/components/LegacySidebar.tsx b/apps/web/src/components/LegacySidebar.tsx
index 13dc5b7c1a7a..3c7da604123d 100644
--- a/apps/web/src/components/LegacySidebar.tsx
+++ b/apps/web/src/components/LegacySidebar.tsx
@@ -909,11 +909,7 @@ export const SidebarThreadRow = memo(function SidebarThreadRow(props: SidebarThr
               >
                 <span
                   data-legacy-sidebar-unscaled-content
-                  className={
-                    props.compactStatusIndicators
-                      ? "size-[9px] rounded-full bg-yellow-500 dark:bg-yellow-300"
-                      : "size-1.5 rounded-full bg-yellow-500 dark:bg-yellow-300"
-                  }
+                  className="size-1.5 rounded-full bg-yellow-500 dark:bg-yellow-300"
                 />
               </TooltipTrigger>
               <TooltipPopup side="top">Waiting for {thread.actionResume.actionName}</TooltipPopup>
diff --git a/apps/web/src/components/Sidebar.tsx b/apps/web/src/components/Sidebar.tsx
index 1379919fee6f..fa92aac8f1c2 100644
--- a/apps/web/src/components/Sidebar.tsx
+++ b/apps/web/src/components/Sidebar.tsx
@@ -628,7 +628,6 @@ const SidebarThreadRow = memo(function SidebarThreadRow(props: {
   environmentLabel: string | null;
   environmentKnown: boolean;
   showLocalEnvironmentIcon: boolean;
-  showWorktreeIndicators: boolean;
   configuredEnvironmentIconColor: EnvironmentIconColor | undefined;
   projectCwd: string | null;
   projectFaviconPath: string | null;
@@ -1622,9 +1621,7 @@ const SidebarThreadRow = memo(function SidebarThreadRow(props: {
                   branch, so the row lost its most stable identifier. */}
               {thread.branch ? (
                 <>
-                  {props.showWorktreeIndicators ? (
-                    <ThreadWorktreeIndicator thread={thread} />
-                  ) : null}
+                  <ThreadWorktreeIndicator thread={thread} />
                   <span className="min-w-0 flex-1 truncate whitespace-nowrap">{thread.branch}</span>
                 </>
               ) : (
@@ -1826,7 +1823,6 @@ export default function Sidebar() {
   const projectGroupingSettings = useClientSettings(selectProjectGroupingSettings);
   const environmentIconColors = useClientSettings((s) => s.environmentIconColors);
   const showLocalEnvironmentIcon = useClientSettings((s) => s.showLocalEnvironmentIcon);
-  const showWorktreeIndicators = useClientSettings((s) => s.showThreadWorktreeIndicators);
   const {
     settleThread,
     unsettleThread,
@@ -3878,7 +3874,6 @@ export default function Sidebar() {
                         environmentLabel={environmentLabelById.get(thread.environmentId) ?? null}
                         environmentKnown={environmentLabelById.has(thread.environmentId)}
                         showLocalEnvironmentIcon={showLocalEnvironmentIcon}
-                        showWorktreeIndicators={showWorktreeIndicators}
                         configuredEnvironmentIconColor={environmentIconColors[thread.environmentId]}
                         projectCwd={
                           projectCwdByKey.get(`${thread.environmentId}:${thread.projectId}`) ?? null
diff --git a/apps/web/src/components/ThreadStatusIndicators.test.tsx b/apps/web/src/components/ThreadStatusIndicators.test.tsx
index 868bd2cd99c0..205cb650cdd9 100644
--- a/apps/web/src/components/ThreadStatusIndicators.test.tsx
+++ b/apps/web/src/components/ThreadStatusIndicators.test.tsx
@@ -2,7 +2,25 @@ import { ThreadId } from "@t3tools/contracts";
 import { renderToStaticMarkup } from "react-dom/server";
 import { describe, expect, it } from "vite-plus/test";
 
-import { ThreadWorktreeIndicator } from "./ThreadStatusIndicators";
+import { ThreadStatusLabel, ThreadWorktreeIndicator } from "./ThreadStatusIndicators";
+
+describe("ThreadStatusLabel", () => {
+  it("keeps the status dot the same size when labels are compacted", () => {
+    const status = {
+      colorClass: "text-sky-600",
+      dotClass: "bg-sky-500",
+      label: "Working",
+      pulse: false,
+    };
+
+    const expandedMarkup = renderToStaticMarkup(<ThreadStatusLabel status={status} />);
+    const compactMarkup = renderToStaticMarkup(<ThreadStatusLabel status={status} compact />);
+
+    expect(expandedMarkup).toContain("size-1.5");
+    expect(compactMarkup).toContain("size-1.5");
+    expect(compactMarkup).not.toContain("size-[9px]");
+  });
+});
 
 describe("ThreadWorktreeIndicator", () => {
   it("renders the worktree folder and branch in an accessible label", () => {
diff --git a/apps/web/src/components/ThreadStatusIndicators.tsx b/apps/web/src/components/ThreadStatusIndicators.tsx
index a94fc5e6e6b0..178a983162dc 100644
--- a/apps/web/src/components/ThreadStatusIndicators.tsx
+++ b/apps/web/src/components/ThreadStatusIndicators.tsx
@@ -369,7 +369,7 @@ export function ThreadStatusLabel({
         >
           <span
             data-legacy-sidebar-unscaled-content
-            className={`size-[9px] rounded-full ${status.dotClass} ${
+            className={`size-1.5 rounded-full ${status.dotClass} ${
               status.pulse ? "animate-status-pulse" : ""
             }`}
           />
@@ -391,7 +391,7 @@ export function ThreadStatusLabel({
       >
         <span
           data-legacy-sidebar-unscaled-content
-          className={`h-1.5 w-1.5 rounded-full ${status.dotClass} ${
+          className={`size-1.5 rounded-full ${status.dotClass} ${
             status.pulse ? "animate-status-pulse" : ""
           }`}
         />
diff --git a/apps/web/src/components/chat/MessagesTimeline.test.tsx b/apps/web/src/components/chat/MessagesTimeline.test.tsx
index d1cc9aa37702..beec7fbb4d75 100644
--- a/apps/web/src/components/chat/MessagesTimeline.test.tsx
+++ b/apps/web/src/components/chat/MessagesTimeline.test.tsx
@@ -391,6 +391,7 @@ describe("MessagesTimeline", () => {
 
     expect(markup).toContain('data-testid="timeline-minimap"');
     expect(markup).toContain("data-thread-annotation-marker");
+    expect(markup).toContain('data-slot="popover-trigger"');
     expect(markup).toContain("[@media(pointer:coarse)]:block");
     expect(markup).toContain("[@media(pointer:coarse)]:opacity-100");
     expect(markup).not.toContain("data-thread-annotation-overflow");
@@ -413,6 +414,7 @@ describe("MessagesTimeline", () => {
 
     expect(markup).toContain("data-thread-annotation-overflow");
     expect(markup).toContain('aria-label="Annotation attached to an earlier message"');
+    expect(markup).toContain('data-slot="popover-trigger"');
     expect(markup).toContain('class="pointer-events-auto absolute left-3"');
     expect(markup).not.toContain("data-thread-annotation-marker");
   });
diff --git a/apps/web/src/components/chat/MessagesTimeline.tsx b/apps/web/src/components/chat/MessagesTimeline.tsx
index 056ca265f59a..920f32f6adcb 100644
--- a/apps/web/src/components/chat/MessagesTimeline.tsx
+++ b/apps/web/src/components/chat/MessagesTimeline.tsx
@@ -95,6 +95,7 @@ import {
 } from "./MessagesTimeline.logic";
 import { TerminalContextInlineChip } from "./TerminalContextInlineChip";
 import { Tooltip, TooltipPopup, TooltipTrigger } from "../ui/tooltip";
+import { Popover, PopoverPopup, PopoverTrigger } from "../ui/popover";
 import {
   deriveDisplayedUserMessageState,
   type ParsedTerminalContextEntry,
@@ -774,6 +775,94 @@ function timelineMinimapEventTargetsPreview(target: EventTarget): boolean {
   return target instanceof Element && target.closest("[data-minimap-preview]") !== null;
 }
 
+function TimelineAnnotationPopover({
+  annotation,
+  ariaLabel,
+  earlier,
+  markdownCwd,
+  open,
+  threadRef,
+  triggerClassName,
+  onActivate,
+  onAnnotationBodyChange,
+  onAnnotationEdit,
+  onAnnotationResolve,
+  onAnnotationReopen,
+  onOpenChange,
+}: {
+  annotation: ThreadAnnotation;
+  ariaLabel: string;
+  earlier: boolean;
+  markdownCwd: string | undefined;
+  open: boolean;
+  threadRef: ScopedThreadRef;
+  triggerClassName: string;
+  onActivate?: () => void;
+  onAnnotationBodyChange: ((body: string) => Promise<boolean>) | undefined;
+  onAnnotationEdit: () => void;
+  onAnnotationResolve: () => void;
+  onAnnotationReopen: () => void;
+  onOpenChange: (open: boolean) => void;
+}) {
+  const annotationBodyPending = useThreadAnnotationBodyPending(threadRef);
+
+  return (
+    <Popover open={open} onOpenChange={onOpenChange}>
+      <PopoverTrigger
+        closeDelay={120}
+        delay={0}
+        openOnHover
+        render={
+          <button
+            aria-label={ariaLabel}
+            className={triggerClassName}
+            data-thread-annotation-marker={earlier ? undefined : ""}
+            type="button"
+          />
+        }
+        onClick={(event) => {
+          event.stopPropagation();
+          onActivate?.();
+        }}
+        onFocus={onActivate}
+      />
+      <PopoverPopup
+        align="center"
+        className="w-80 max-w-80 text-left shadow-xl shadow-black/25 before:hidden"
+        data-minimap-preview
+        finalFocus={false}
+        initialFocus={false}
+        side="right"
+        tooltipStyle
+        viewportClassName="p-0"
+      >
+        <div className="w-80 max-w-80 bg-warning/10 p-3 text-warning-foreground">
+          {earlier ? (
+            <div className="mb-2 text-[11px] font-medium">Attached to an earlier message</div>
+          ) : null}
+          <ThreadAnnotationBody
+            annotation={annotation}
+            className="max-h-52 overflow-y-auto"
+            compact
+            cwd={markdownCwd}
+            onBodyChange={onAnnotationBodyChange}
+            threadRef={threadRef}
+          />
+          <div className="mt-2">
+            <ThreadAnnotationActions
+              annotation={annotation}
+              onEdit={onAnnotationEdit}
+              onReopen={onAnnotationReopen}
+              onResolve={onAnnotationResolve}
+              pending={annotationBodyPending}
+            />
+          </div>
+        </div>
+      </PopoverPopup>
+    </Popover>
+  );
+}
+
 function TimelineMinimap({
   annotation,
   hasPersistentGutter,
@@ -801,9 +890,8 @@ function TimelineMinimap({
   onAnnotationReopen: () => void;
   onSelect: (item: TimelineMinimapItem) => void;
 }) {
-  const annotationBodyPending = useThreadAnnotationBodyPending(threadRef);
   const [activeIndex, setActiveIndex] = useState<number | null>(null);
-  const [overflowAnnotationOpen, setOverflowAnnotationOpen] = useState(false);
+  const [annotationPopoverOpen, setAnnotationPopoverOpen] = useState(false);
 
   const resolvedActiveIndex =
     activeIndex !== null && activeIndex < items.length ? activeIndex : null;
@@ -812,8 +900,6 @@ function TimelineMinimap({
     ? items.findIndex((item) => item.messageId === annotation.anchorMessageId)
     : -1;
   const annotationIsEarlier = annotation !== null && annotationItemIndex === -1;
-  const activeItemHasAnnotation =
-    annotation !== null && activeItem?.messageId === annotation.anchorMessageId;
   const activeTopPercent =
     resolvedActiveIndex === null
       ? 0
@@ -904,6 +990,9 @@ function TimelineMinimap({
           }}
           onFocus={() => setActiveIndex((current) => current ?? 0)}
           onKeyDown={(event) => {
+            if (timelineMinimapEventTargetsPreview(event.target)) {
+              return;
+            }
             if (event.key === "ArrowDown") {
               event.preventDefault();
               moveActiveIndex(1);
@@ -970,23 +1059,27 @@ function TimelineMinimap({
                 }}
                 style={{ top }}
               >
-                {annotation?.anchorMessageId === item.messageId ? (
-                  <button
-                    aria-label="Thread annotation"
-                    className="pointer-events-auto absolute left-full top-1/2 ml-1 size-1.5 -translate-y-1/2 rounded-full bg-warning ring-1 ring-background/70"
-                    data-thread-annotation-marker
-                    type="button"
-                    onClick={(event) => {
-                      event.stopPropagation();
-                      setActiveIndex(index);
-                    }}
-                    onFocus={() => setActiveIndex(index)}
+                {annotation?.anchorMessageId === item.messageId && threadRef ? (
+                  <TimelineAnnotationPopover
+                    annotation={annotation}
+                    ariaLabel="Thread annotation"
+                    earlier={false}
+                    markdownCwd={markdownCwd}
+                    open={annotationPopoverOpen}
+                    threadRef={threadRef}
+                    triggerClassName="pointer-events-auto absolute left-full top-1/2 ml-1 size-1.5 -translate-y-1/2 rounded-full bg-warning ring-1 ring-background/70"
+                    onActivate={() => setActiveIndex(index)}
+                    onAnnotationBodyChange={onAnnotationBodyChange}
+                    onAnnotationEdit={onAnnotationEdit}
+                    onAnnotationReopen={onAnnotationReopen}
+                    onAnnotationResolve={onAnnotationResolve}
+                    onOpenChange={setAnnotationPopoverOpen}
                   />
                 ) : null}
               </span>
             );
           })}
-          {activeItem ? (
+          {activeItem && !annotationPopoverOpen ? (
             <span
               className="pointer-events-auto absolute left-8 w-80 cursor-text select-text"
               data-minimap-preview
@@ -996,45 +1089,23 @@ function TimelineMinimap({
                 transform: `translateY(${activeTooltipTranslate})`,
               }}
             >
-              {activeItemHasAnnotation && annotation && threadRef ? (
-                <span className="block rounded-xl border border-border/80 bg-warning/10 p-3 text-left text-warning-foreground shadow-xl shadow-black/25">
-                  <ThreadAnnotationBody
-                    annotation={annotation}
-                    className="max-h-52 overflow-y-auto"
-                    compact
-                    cwd={markdownCwd}
-                    onBodyChange={onAnnotationBodyChange}
-                    threadRef={threadRef}
-                  />
-                  <span className="mt-2 block">
-                    <ThreadAnnotationActions
-                      annotation={annotation}
-                      onEdit={onAnnotationEdit}
-                      onReopen={onAnnotationReopen}
-                      onResolve={onAnnotationResolve}
-                      pending={annotationBodyPending}
-                    />
-                  </span>
+              <span className="dropdown-glass block rounded-xl p-3 text-left text-popover-foreground shadow-xl shadow-black/25">
+                <span className="block max-w-full overflow-hidden text-ellipsis whitespace-nowrap text-sm font-medium leading-5">
+                  {activeItem.userText ?? "User message"}
                 </span>
-              ) : (
-                <span className="dropdown-glass block rounded-xl p-3 text-left text-popover-foreground shadow-xl shadow-black/25">
-                  <span className="block max-w-full overflow-hidden text-ellipsis whitespace-nowrap text-sm font-medium leading-5">
-                    {activeItem.userText ?? "User message"}
+                {activeItem.assistantText ? (
+                  <span
+                    className="mt-1 max-h-[3.75rem] overflow-hidden text-muted-foreground text-sm leading-5"
+                    style={{
+                      display: "-webkit-box",
+                      WebkitBoxOrient: "vertical",
+                      WebkitLineClamp: 3,
+                    }}
+                  >
+                    {activeItem.assistantText}
                   </span>
-                  {activeItem.assistantText ? (
-                    <span
-                      className="mt-1 max-h-[3.75rem] overflow-hidden text-muted-foreground text-sm leading-5"
-                      style={{
-                        display: "-webkit-box",
-                        WebkitBoxOrient: "vertical",
-                        WebkitLineClamp: 3,
-                      }}
-                    >
-                      {activeItem.assistantText}
-                    </span>
-                  ) : null}
-                </span>
-              )}
+                ) : null}
+              </span>
             </span>
           ) : null}
         </div>
@@ -1042,49 +1113,25 @@ function TimelineMinimap({
           <div
             className="pointer-events-auto absolute left-3"
             data-thread-annotation-overflow
-            onMouseEnter={() => setOverflowAnnotationOpen(true)}
-            onMouseLeave={() => setOverflowAnnotationOpen(false)}
-            onBlurCapture={(event) => {
-              if (!event.currentTarget.contains(event.relatedTarget)) {
-                setOverflowAnnotationOpen(false);
-              }
-            }}
             style={{
               top: "50%",
               transform: `translateY(calc(-50% - ${resolveTimelineMinimapHeightStyle(items.length)} / 2))`,
             }}
           >
-            <button
-              aria-label="Annotation attached to an earlier message"
-              className="size-1.5 rounded-full bg-warning ring-1 ring-background/70"
-              type="button"
-              onClick={() => setOverflowAnnotationOpen((open) => !open)}
-              onFocus={() => setOverflowAnnotationOpen(true)}
+            <TimelineAnnotationPopover
+              annotation={annotation}
+              ariaLabel="Annotation attached to an earlier message"
+              earlier
+              markdownCwd={markdownCwd}
+              open={annotationPopoverOpen}
+              threadRef={threadRef}
+              triggerClassName="size-1.5 rounded-full bg-warning ring-1 ring-background/70"
+              onAnnotationBodyChange={onAnnotationBodyChange}
+              onAnnotationEdit={onAnnotationEdit}
+              onAnnotationReopen={onAnnotationReopen}
+              onAnnotationResolve={onAnnotationResolve}
+              onOpenChange={setAnnotationPopoverOpen}
             />
-            {overflowAnnotationOpen ? (
-              <div className="absolute left-5 top-0 w-80 -translate-y-1/2 rounded-xl border border-border/80 bg-warning/10 p-3 text-left text-warning-foreground shadow-xl shadow-black/25">
-                <div className="mb-2 text-[11px] font-medium text-warning-foreground">
-                  Attached to an earlier message
-                </div>
-                <ThreadAnnotationBody
-                  annotation={annotation}
-                  className="max-h-52 overflow-y-auto"
-                  compact
-                  cwd={markdownCwd}
-                  onBodyChange={onAnnotationBodyChange}
-                  threadRef={threadRef}
-                />
-                <div className="mt-2">
-                  <ThreadAnnotationActions
-                    annotation={annotation}
-                    onEdit={onAnnotationEdit}
-                    onReopen={onAnnotationReopen}
-                    onResolve={onAnnotationResolve}
-                    pending={annotationBodyPending}
-                  />
-                </div>
-              </div>
-            ) : null}
           </div>
         ) : null}
       </div>
diff --git a/apps/web/src/components/settings/LastCodeSettings.tsx b/apps/web/src/components/settings/LastCodeSettings.tsx
index cb8e80beb58c..22e54adc03cb 100644
--- a/apps/web/src/components/settings/LastCodeSettings.tsx
+++ b/apps/web/src/components/settings/LastCodeSettings.tsx
@@ -1,6 +1,7 @@
-import type {
+import {
   DesktopLastCodeSettingsState,
   LastCodeSettingsImportPreview,
+  ThreadId,
 } from "@t3tools/contracts";
 import {
   DEFAULT_LEGACY_SIDEBAR_SCALE,
@@ -21,6 +22,7 @@ import { usePrimaryEnvironmentId } from "../../state/environments";
 import { Button } from "../ui/button";
 import { Switch } from "../ui/switch";
 import { stackedThreadToast, toastManager } from "../ui/toast";
+import { ThreadStatusLabel, ThreadWorktreeIndicator } from "../ThreadStatusIndicators";
 import { searchableSetting } from "./settingsSearch";
 import { ProviderAccentColorPicker } from "./ProviderAccentColorPicker";
 import { deriveLastCodeEnvironmentSettingEntries } from "./LastCodeSettings.logic";
@@ -31,6 +33,19 @@ import {
   SettingsSection,
 } from "./settingsLayout";
 
+const STATUS_INDICATOR_PREVIEW = {
+  colorClass: "text-sky-600 dark:text-sky-300/80",
+  dotClass: "bg-sky-500 dark:bg-sky-300/80",
+  label: "Working",
+  pulse: false,
+} as const;
+
+const WORKTREE_INDICATOR_PREVIEW_THREAD = {
+  id: ThreadId.make("settings-worktree-preview"),
+  branch: "feature/example",
+  worktreePath: "/example/worktrees/example",
+};
+
 export function LastCodeSettingsPanel() {
   const updateState = useDesktopUpdateState();
   const clientSettings = usePrimarySettings();
@@ -237,6 +252,15 @@ export function LastCodeSettingsPanel() {
         <SettingsRow
           {...searchableSetting("compact-status-indicators")}
           description="Show colored dot only for agent status, hiding labels like “Working” and “Completed.”"
+          status={
+            <span className="inline-flex items-center gap-1.5 rounded-full bg-sidebar px-2 py-1 text-sm text-foreground">
+              <ThreadStatusLabel
+                compact={clientSettings.compactLegacySidebarStatuses}
+                status={STATUS_INDICATOR_PREVIEW}
+              />
+              <span>Title</span>
+            </span>
+          }
           control={
             <Switch
               checked={clientSettings.compactLegacySidebarStatuses}
@@ -249,14 +273,23 @@ export function LastCodeSettingsPanel() {
         />
         <SettingsRow
           {...searchableSetting("show-worktree-indicators")}
-          description="Show the worktree icon beside threads that use a dedicated worktree."
+          description="Show the worktree icon beside threads that use a dedicated worktree in the legacy sidebar."
+          status={
+            <span className="inline-flex items-center gap-1 rounded-full bg-sidebar px-2 py-1 text-[10px] tabular-nums text-secondary-label">
+              {clientSettings.showThreadWorktreeIndicators ? (
+                <ThreadWorktreeIndicator thread={WORKTREE_INDICATOR_PREVIEW_THREAD} />
+              ) : null}
+              <EnvironmentIcon kind="server" context="legacy-row" className="size-3" />
+              <span>5m ago</span>
+            </span>
+          }
           control={
             <Switch
               checked={clientSettings.showThreadWorktreeIndicators}
               onCheckedChange={(checked) =>
                 updateClientSettings({ showThreadWorktreeIndicators: Boolean(checked) })
               }
-              aria-label="Show worktree indicators"
+              aria-label="Show worktree indicators (legacy sidebar)"
             />
           }
         />
diff --git a/apps/web/src/components/settings/settingsSearch.test.ts b/apps/web/src/components/settings/settingsSearch.test.ts
index 4255680873cd..e18ccbbf2e45 100644
--- a/apps/web/src/components/settings/settingsSearch.test.ts
+++ b/apps/web/src/components/settings/settingsSearch.test.ts
@@ -79,6 +79,10 @@ describe("searchSettings", () => {
   it("serves anchor props to panels from the catalog", () => {
     expect(searchableSetting("word-wrap")).toEqual({ id: "word-wrap", title: "Word wrap" });
     expect(searchableSetting("archive")).toEqual({ id: "archive", title: "Archived threads" });
+    expect(searchableSetting("show-worktree-indicators")).toEqual({
+      id: "show-worktree-indicators",
+      title: "Show worktree indicators (legacy sidebar)",
+    });
   });
 
   it("routes appearance settings to their current section", () => {
diff --git a/apps/web/src/components/settings/settingsSearch.ts b/apps/web/src/components/settings/settingsSearch.ts
index 5e4cf898e4f0..52f56153e561 100644
--- a/apps/web/src/components/settings/settingsSearch.ts
+++ b/apps/web/src/components/settings/settingsSearch.ts
@@ -267,7 +267,7 @@ export const SETTINGS_SEARCH_ITEMS = [
   },
   {
     id: "show-worktree-indicators",
-    title: "Show worktree indicators",
+    title: "Show worktree indicators (legacy sidebar)",
     to: "/settings/lastcode",
   },
   {