diff --git a/packages/app/src/components/sidebar-workspace-list.tsx b/packages/app/src/components/sidebar-workspace-list.tsx
index c47eaf14a..4086cd384 100644
--- a/packages/app/src/components/sidebar-workspace-list.tsx
+++ b/packages/app/src/components/sidebar-workspace-list.tsx
@@ -64,6 +64,7 @@ import {
   parseHostWorkspaceRouteFromPathname,
 } from "@/utils/host-routes";
 import {
+  shouldShowSidebarHostLabels,
   useSidebarWorkspaceEntry,
   type SidebarProjectEntry,
   type SidebarStatusWorkspacePlacement,
@@ -1879,6 +1880,7 @@ function ProjectBlock({
   creatingWorkspaceIds,
   activeWorkspaceSelection,
   hostLabelByServerId,
+  showHostLabels,
 }: {
   project: SidebarProjectEntry;
   collapsed: boolean;
@@ -1899,6 +1901,7 @@ function ProjectBlock({
   creatingWorkspaceIds: ReadonlySet<string>;
   activeWorkspaceSelection: ActiveWorkspaceSelection | null;
   hostLabelByServerId: ReadonlyMap<string, string>;
+  showHostLabels: boolean;
 }) {
   const rowModel = useMemo(
     () =>
@@ -1928,9 +1931,7 @@ function ProjectBlock({
         <MemoWorkspaceRowItem
           workspace={item}
           subtitle={
-            project.hosts.length > 1
-              ? (hostLabelByServerId.get(item.serverId) ?? item.serverId)
-              : null
+            showHostLabels ? (hostLabelByServerId.get(item.serverId) ?? item.serverId) : null
           }
           shortcutNumber={shortcutIndexByWorkspaceKey.get(item.workspaceKey) ?? null}
           showShortcutBadge={showShortcutBadges}
@@ -1947,7 +1948,7 @@ function ProjectBlock({
     },
     [
       project.projectKind,
-      project.hosts.length,
+      showHostLabels,
       activeWorkspaceSelection,
       creatingWorkspaceIds,
       hostLabelByServerId,
@@ -2115,6 +2116,7 @@ function areProjectBlockPropsEqual(previous: ProjectBlockProps, next: ProjectBlo
     previous.showShortcutBadges === next.showShortcutBadges &&
     previous.shortcutIndexByWorkspaceKey === next.shortcutIndexByWorkspaceKey &&
     previous.hostLabelByServerId === next.hostLabelByServerId &&
+    previous.showHostLabels === next.showHostLabels &&
     previous.parentGestureRef === next.parentGestureRef &&
     previous.onToggleCollapsed === next.onToggleCollapsed &&
     previous.onWorkspacePress === next.onWorkspacePress &&
@@ -2181,6 +2183,7 @@ export function SidebarWorkspaceList({
     }
     return labels;
   }, [hosts]);
+  const showHostLabels = useMemo(() => shouldShowSidebarHostLabels(projects), [projects]);
 
   const content =
     groupMode === "status" ? (
@@ -2189,6 +2192,8 @@ export function SidebarWorkspaceList({
         projectNamesByKey={projectNamesByKey}
         shortcutIndexByWorkspaceKey={shortcutIndexByWorkspaceKey}
         onWorkspacePress={onWorkspacePress}
+        hostLabelByServerId={hostLabelByServerId}
+        showHostLabels={showHostLabels}
       />
     ) : (
       <ProjectModeList
@@ -2202,6 +2207,7 @@ export function SidebarWorkspaceList({
         parentGestureRef={parentGestureRef}
         pathname={pathname}
         hostLabelByServerId={hostLabelByServerId}
+        showHostLabels={showHostLabels}
       />
     );
 
@@ -2213,11 +2219,15 @@ function SidebarStatusModeWrapper({
   projectNamesByKey,
   shortcutIndexByWorkspaceKey: _projectShortcutIndex,
   onWorkspacePress,
+  hostLabelByServerId,
+  showHostLabels,
 }: {
   statusWorkspacePlacements: SidebarStatusWorkspacePlacement[];
   projectNamesByKey: Map<string, string>;
   shortcutIndexByWorkspaceKey: Map<string, number>;
   onWorkspacePress?: () => void;
+  hostLabelByServerId: ReadonlyMap<string, string>;
+  showHostLabels: boolean;
 }) {
   const showShortcutBadges = useShowShortcutBadges();
 
@@ -2228,6 +2238,8 @@ function SidebarStatusModeWrapper({
       shortcutIndexByWorkspaceKey={_projectShortcutIndex}
       showShortcutBadges={showShortcutBadges}
       onWorkspacePress={onWorkspacePress}
+      hostLabelByServerId={hostLabelByServerId}
+      showHostLabels={showHostLabels}
     />
   );
 }
@@ -2243,12 +2255,14 @@ function ProjectModeList({
   parentGestureRef,
   pathname,
   hostLabelByServerId,
+  showHostLabels,
 }: Omit<
   SidebarWorkspaceListProps,
   "statusWorkspacePlacements" | "projectNamesByKey" | "groupMode" | "isRefreshing" | "onRefresh"
 > & {
   pathname: string;
   hostLabelByServerId: ReadonlyMap<string, string>;
+  showHostLabels: boolean;
 }) {
   const { t } = useTranslation();
   const [creatingWorkspaceIds, setCreatingWorkspaceIds] = useState<Set<string>>(() => new Set());
@@ -2436,6 +2450,7 @@ function ProjectModeList({
           creatingWorkspaceIds={creatingWorkspaceIds}
           activeWorkspaceSelection={activeWorkspaceSelection}
           hostLabelByServerId={hostLabelByServerId}
+          showHostLabels={showHostLabels}
         />
       );
     },
@@ -2445,6 +2460,7 @@ function ProjectModeList({
       handleWorktreeCreated,
       handleWorkspaceReorder,
       hostLabelByServerId,
+      showHostLabels,
       onWorkspacePress,
       onToggleProjectCollapsed,
       parentGestureRef,
diff --git a/packages/app/src/components/sidebar/sidebar-status-list.tsx b/packages/app/src/components/sidebar/sidebar-status-list.tsx
index bd39e2b9d..3b506647c 100644
--- a/packages/app/src/components/sidebar/sidebar-status-list.tsx
+++ b/packages/app/src/components/sidebar/sidebar-status-list.tsx
@@ -95,6 +95,8 @@ interface StatusWorkspaceListProps {
   shortcutIndexByWorkspaceKey: Map<string, number>;
   showShortcutBadges: boolean;
   onWorkspacePress?: () => void;
+  hostLabelByServerId: ReadonlyMap<string, string>;
+  showHostLabels: boolean;
 }
 
 export function SidebarStatusWorkspaceList({
@@ -103,6 +105,8 @@ export function SidebarStatusWorkspaceList({
   shortcutIndexByWorkspaceKey: _projectShortcutIndex,
   showShortcutBadges,
   onWorkspacePress,
+  hostLabelByServerId,
+  showHostLabels,
 }: StatusWorkspaceListProps) {
   const groups = useMemo(
     () => buildStatusGroups(workspaces, projectNamesByKey),
@@ -138,6 +142,8 @@ export function SidebarStatusWorkspaceList({
             shortcutIndex={statusShortcutIndex}
             showShortcutBadges={showShortcutBadges}
             onWorkspacePress={onWorkspacePress}
+            hostLabelByServerId={hostLabelByServerId}
+            showHostLabels={showHostLabels}
           />
         </NestableScrollContainer>
       ) : (
@@ -154,6 +160,8 @@ export function SidebarStatusWorkspaceList({
             shortcutIndex={statusShortcutIndex}
             showShortcutBadges={showShortcutBadges}
             onWorkspacePress={onWorkspacePress}
+            hostLabelByServerId={hostLabelByServerId}
+            showHostLabels={showHostLabels}
           />
         </ScrollView>
       )}
@@ -168,6 +176,8 @@ function StatusGroupList({
   shortcutIndex,
   showShortcutBadges,
   onWorkspacePress,
+  hostLabelByServerId,
+  showHostLabels,
 }: {
   groups: StatusGroup[];
   collapsedStatusGroupKeys: ReadonlySet<string>;
@@ -175,6 +185,8 @@ function StatusGroupList({
   shortcutIndex: Map<string, number>;
   showShortcutBadges: boolean;
   onWorkspacePress?: () => void;
+  hostLabelByServerId: ReadonlyMap<string, string>;
+  showHostLabels: boolean;
 }) {
   return (
     <>
@@ -190,7 +202,12 @@ function StatusGroupList({
                 <StatusWorkspaceRow
                   key={workspace.workspaceKey}
                   workspace={workspace}
-                  projectName={projectNamesByKey.get(workspace.projectKey) ?? ""}
+                  subtitle={buildStatusRowSubtitle({
+                    projectName: projectNamesByKey.get(workspace.projectKey) ?? "",
+                    hostLabel: showHostLabels
+                      ? (hostLabelByServerId.get(workspace.serverId) ?? workspace.serverId)
+                      : null,
+                  })}
                   shortcutNumber={shortcutIndex.get(workspace.workspaceKey) ?? null}
                   showShortcutBadge={showShortcutBadges}
                   onWorkspacePress={onWorkspacePress}
@@ -204,6 +221,21 @@ function StatusGroupList({
   );
 }
 
+// Status mode breaks the project grouping, so the row needs the project name to stay
+// legible; the host is appended after a middle dot once labels are active.
+function buildStatusRowSubtitle({
+  projectName,
+  hostLabel,
+}: {
+  projectName: string;
+  hostLabel: string | null;
+}): string {
+  if (!hostLabel) {
+    return projectName;
+  }
+  return projectName ? `${projectName} · ${hostLabel}` : hostLabel;
+}
+
 function StatusGroupHeader({ group, collapsed }: { group: StatusGroup; collapsed: boolean }) {
   const [isHovered, setIsHovered] = useState(false);
   const toggleStatusGroupCollapsed = useSidebarCollapsedSectionsStore(
@@ -288,13 +320,13 @@ function StatusGroupIcon({ bucket }: { bucket: StatusGroup["bucket"] }) {
 
 const StatusWorkspaceRow = memo(function StatusWorkspaceRow({
   workspace,
-  projectName,
+  subtitle,
   shortcutNumber,
   showShortcutBadge,
   onWorkspacePress,
 }: {
   workspace: SidebarStatusWorkspacePlacement;
-  projectName: string;
+  subtitle: string;
   shortcutNumber: number | null;
   showShortcutBadge: boolean;
   onWorkspacePress?: () => void;
@@ -316,7 +348,7 @@ const StatusWorkspaceRow = memo(function StatusWorkspaceRow({
   return (
     <StatusWorkspaceRowWithMenu
       workspace={workspaceEntry}
-      projectName={projectName}
+      subtitle={subtitle}
       selected={selected}
       shortcutNumber={shortcutNumber}
       showShortcutBadge={showShortcutBadge}
@@ -327,14 +359,14 @@ const StatusWorkspaceRow = memo(function StatusWorkspaceRow({
 
 function StatusWorkspaceRowWithMenu({
   workspace,
-  projectName,
+  subtitle,
   selected,
   shortcutNumber,
   showShortcutBadge,
   onPress,
 }: {
   workspace: SidebarWorkspaceEntry;
-  projectName: string;
+  subtitle: string;
   selected: boolean;
   shortcutNumber: number | null;
   showShortcutBadge: boolean;
@@ -455,7 +487,7 @@ function StatusWorkspaceRowWithMenu({
     <>
       <StatusWorkspaceRowInner
         workspace={workspace}
-        projectName={projectName}
+        subtitle={subtitle}
         selected={selected}
         shortcutNumber={shortcutNumber}
         showShortcutBadge={showShortcutBadge}
@@ -487,7 +519,7 @@ function StatusWorkspaceRowWithMenu({
 
 function StatusWorkspaceRowInner({
   workspace,
-  projectName,
+  subtitle,
   selected,
   shortcutNumber,
   showShortcutBadge,
@@ -504,7 +536,7 @@ function StatusWorkspaceRowInner({
   archiveShortcutKeys,
 }: {
   workspace: SidebarWorkspaceEntry;
-  projectName: string;
+  subtitle: string;
   selected: boolean;
   shortcutNumber: number | null;
   showShortcutBadge: boolean;
@@ -554,7 +586,7 @@ function StatusWorkspaceRowInner({
             >
               <SidebarWorkspaceRowContent
                 workspace={workspace}
-                subtitle={projectName}
+                subtitle={subtitle}
                 scriptIconKind={scriptIconKind}
                 isHovered={isHovered}
                 isLoading={isArchiving}
diff --git a/packages/app/src/hooks/sidebar-workspaces-view-model.test.ts b/packages/app/src/hooks/sidebar-workspaces-view-model.test.ts
index 4e827b3ca..0c86599f7 100644
--- a/packages/app/src/hooks/sidebar-workspaces-view-model.test.ts
+++ b/packages/app/src/hooks/sidebar-workspaces-view-model.test.ts
@@ -9,6 +9,7 @@ import {
   buildSidebarProjectsFromStructure,
   computeSidebarOrderUpdates,
   deriveSidebarLoadingState,
+  shouldShowSidebarHostLabels,
   type SidebarProjectEntry,
 } from "./sidebar-workspaces-view-model";
 
@@ -297,6 +298,63 @@ describe("shared sidebar workspace model", () => {
   });
 });
 
+describe("shouldShowSidebarHostLabels", () => {
+  it("is false with no visible projects", () => {
+    expect(shouldShowSidebarHostLabels([])).toBe(false);
+  });
+
+  it("is false when every project lives on a single host", () => {
+    const projects = buildSidebarProjectsFromStructure({
+      projects: [
+        project({ projectKey: "project-a", workspaceKeys: ["ws-1"] }),
+        project({ projectKey: "project-b", workspaceKeys: ["ws-2"] }),
+      ],
+    });
+
+    expect(shouldShowSidebarHostLabels(projects)).toBe(false);
+  });
+
+  it("is true when projects span separate hosts", () => {
+    const projects = buildSidebarProjectsFromStructure({
+      projects: [
+        project({
+          projectKey: "project-a",
+          hosts: [
+            { serverId: "host-a", iconWorkingDir: "/repo/project-a", canCreateWorktree: true },
+          ],
+          workspaceKeys: ["host-a:ws-1"],
+        }),
+        project({
+          projectKey: "project-b",
+          hosts: [
+            { serverId: "host-b", iconWorkingDir: "/repo/project-b", canCreateWorktree: true },
+          ],
+          workspaceKeys: ["host-b:ws-2"],
+        }),
+      ],
+    });
+
+    expect(shouldShowSidebarHostLabels(projects)).toBe(true);
+  });
+
+  it("is true for a single project shared across hosts", () => {
+    const projects = buildSidebarProjectsFromStructure({
+      projects: [
+        project({
+          projectKey: "getpaseo/paseo",
+          hosts: [
+            { serverId: "host-a", iconWorkingDir: "/repo/paseo", canCreateWorktree: true },
+            { serverId: "host-b", iconWorkingDir: "/repo/paseo", canCreateWorktree: true },
+          ],
+          workspaceKeys: ["host-a:main", "host-b:feature"],
+        }),
+      ],
+    });
+
+    expect(shouldShowSidebarHostLabels(projects)).toBe(true);
+  });
+});
+
 describe("computeSidebarOrderUpdates", () => {
   it("returns no updates when there are no visible projects", () => {
     const updates = computeSidebarOrderUpdates({
diff --git a/packages/app/src/hooks/sidebar-workspaces-view-model.ts b/packages/app/src/hooks/sidebar-workspaces-view-model.ts
index 393c20c0d..dccf4e9e3 100644
--- a/packages/app/src/hooks/sidebar-workspaces-view-model.ts
+++ b/packages/app/src/hooks/sidebar-workspaces-view-model.ts
@@ -351,6 +351,20 @@ export function buildSidebarProjectsFromHostProjects(input: {
   }));
 }
 
+// Host labels disambiguate which machine a workspace lives on; they only earn their
+// space once the visible sidebar spans more than one host. Counting distinct hosts
+// across the visible projects (not all connected hosts) keeps labels off when a host
+// filter pins the view to a single host.
+export function shouldShowSidebarHostLabels(projects: SidebarProjectEntry[]): boolean {
+  const serverIds = new Set<string>();
+  for (const project of projects) {
+    for (const host of project.hosts) {
+      serverIds.add(host.serverId);
+    }
+  }
+  return serverIds.size >= 2;
+}
+
 export function applyStoredOrdering<T>(input: {
   items: T[];
   storedOrder: string[];
diff --git a/packages/app/src/hooks/use-sidebar-workspaces-list.ts b/packages/app/src/hooks/use-sidebar-workspaces-list.ts
index af3def5b3..d02f8a945 100644
--- a/packages/app/src/hooks/use-sidebar-workspaces-list.ts
+++ b/packages/app/src/hooks/use-sidebar-workspaces-list.ts
@@ -31,6 +31,7 @@ export {
   computeSidebarOrderUpdates,
   createSidebarWorkspaceEntry,
   deriveSidebarLoadingState,
+  shouldShowSidebarHostLabels,
   type SidebarLoadingState,
   type SidebarOrderUpdates,
   type SidebarStatusWorkspacePlacement,