diff --git a/apps/desktop/src/app/chat/sidebar/gateway-groups.test.tsx b/apps/desktop/src/app/chat/sidebar/gateway-groups.test.tsx
index c53143c270..4176503eab 100644
--- a/apps/desktop/src/app/chat/sidebar/gateway-groups.test.tsx
+++ b/apps/desktop/src/app/chat/sidebar/gateway-groups.test.tsx
@@ -83,18 +83,37 @@ it('keeps equal profile names on separate gateways and routes section creation a
       .closest('[data-gateway-group]')
       ?.getAttribute('data-gateway-group')
   ).toBe(JSON.stringify([null, 'default']))
-  expect(screen.getByText('This computer · default')).toBeTruthy()
-  expect(screen.getByText('Homelab · default')).toBeTruthy()
-  expect(screen.getByText('Cloud workspace · default')).toBeTruthy()
-  fireEvent.click(screen.getByRole('button', { name: 'New session in Homelab · default' }))
+  act(() =>
+    $sessions.set([
+      ...$sessions.get(),
+      makeSessionInfo({
+        id: 'remote-work',
+        connection_id: 'remote-1',
+        profile: 'work',
+        title: 'Work session',
+        last_active: Date.now() / 1000
+      })
+    ])
+  )
+  const gateway = screen.getByText('Homelab').closest('[data-gateway-section]') as HTMLElement
+  expect(within(gateway).getByText('default')).toBeTruthy()
+  expect(within(gateway).getByText('work')).toBeTruthy()
+  expect(gateway.querySelectorAll('[data-gateway-group]')).toHaveLength(2)
+  fireEvent.click(within(gateway).getAllByRole('button', { name: 'New session in default' })[0])
   expect($newChatRoute.get()).toMatchObject({ connectionId: 'remote-1', profile: 'default' })
   fireEvent.click(screen.getByText('cloud-1 session'))
   expect(resume).toHaveBeenLastCalledWith(
     'cloud-1',
     expect.objectContaining({ connection_id: 'cloud-1', profile: 'default' })
   )
-  const group = screen.getByText('Homelab · default').closest('[data-gateway-group]')!
-  fireEvent.click(within(group as HTMLElement).getByRole('button', { name: 'Hide Homelab · default sessions' }))
+  const group = within(gateway).getByText('default').closest('[data-gateway-group]')!
+  fireEvent.click(within(group as HTMLElement).getByRole('button', { name: 'Hide default sessions' }))
+  expect(screen.queryByText('remote-1 session')).toBeNull()
+  expect(screen.getByText('Work session')).toBeTruthy()
+  fireEvent.click(within(gateway).getByRole('button', { name: 'Hide Homelab sessions' }))
+  expect(screen.queryByText('Work session')).toBeNull()
+  fireEvent.click(within(gateway).getByRole('button', { name: 'Show Homelab sessions' }))
+  expect(screen.getByText('Work session')).toBeTruthy()
   expect(screen.queryByText('remote-1 session')).toBeNull()
   expect(screen.getByText('local session')).toBeTruthy()
 })
diff --git a/apps/desktop/src/app/chat/sidebar/gateway-groups.tsx b/apps/desktop/src/app/chat/sidebar/gateway-groups.tsx
index 07bc128a6a..82281dcd41 100644
--- a/apps/desktop/src/app/chat/sidebar/gateway-groups.tsx
+++ b/apps/desktop/src/app/chat/sidebar/gateway-groups.tsx
@@ -21,6 +21,7 @@ import { ProfileGlyph } from '@/components/ui/profile-glyph'
 import type { SessionInfo } from '@/hermes'
 import { useI18n } from '@/i18n'
 import { useStoreSelector } from '@/lib/use-session-slice'
+import { $connectionsRegistry } from '@/store/connection-registry-state'
 import { newSessionInAgent, newSessionInProfile } from '@/store/profile'
 import { $sessionProfilesUsage } from '@/store/session'
 import { $sidebarSessionRankIds } from '@/store/sidebar-sort'
@@ -45,12 +46,49 @@ interface GatewayProfileGroupsProps {
   renderRows: (sessions: SessionInfo[]) => ReactNode
   sensors?: ReturnType<typeof useSensors>
   onNewSessionSplit?: NewSessionSplitHandler
+  nested?: boolean
 }
 
-export function GatewayProfileGroups({ groups, renderRows, sensors, onNewSessionSplit }: GatewayProfileGroupsProps) {
+export function GatewayProfileGroups({
+  groups,
+  renderRows,
+  sensors,
+  onNewSessionSplit,
+  nested = false
+}: GatewayProfileGroupsProps) {
+  const registry = useStore($connectionsRegistry)
   const order = useStore($gatewayGroupOrder)
+  const gatewayProfiles = new Map<string, SidebarSessionGroup[]>()
+  const sections: SidebarSessionGroup[] = []
 
-  const ordered = [...groups].sort((a, b) => {
+  for (const group of groups) {
+    // Unknown legacy ownership stays unassigned; never guess a local gateway.
+    if (nested || !group.connectionId) {
+      sections.push(nested ? { ...group, label: group.profile! } : group)
+
+      continue
+    }
+
+    const id = JSON.stringify(['gateway', group.connectionId])
+    const profiles = gatewayProfiles.get(id)
+
+    if (profiles) {
+      profiles.push(group)
+    } else {
+      gatewayProfiles.set(id, [group])
+      sections.push({
+        id,
+        connectionId: group.connectionId,
+        label:
+          registry?.connections.find(connection => connection.id === group.connectionId)?.label || group.connectionId,
+        mode: 'profile',
+        path: null,
+        sessions: []
+      })
+    }
+  }
+
+  const ordered = [...sections].sort((a, b) => {
     const left = order.indexOf(a.id)
     const right = order.indexOf(b.id)
 
@@ -70,7 +108,19 @@ export function GatewayProfileGroups({ groups, renderRows, sensors, onNewSession
           onMove={direction => reorderGatewayGroups(arrayMove(ids, index, index + direction))}
           onNewSessionSplit={onNewSessionSplit}
           renderRows={renderRows}
-        />
+        >
+          {gatewayProfiles.has(group.id) && (
+            <div className="ml-3 border-l border-border/50 pl-1">
+              <GatewayProfileGroups
+                groups={gatewayProfiles.get(group.id)!}
+                nested
+                onNewSessionSplit={onNewSessionSplit}
+                renderRows={renderRows}
+                sensors={sensors}
+              />
+            </div>
+          )}
+        </GatewayProfileGroup>
       ))}
     </ReorderableList>
   )
@@ -83,9 +133,18 @@ interface GatewayProfileGroupProps {
   onNewSessionSplit?: NewSessionSplitHandler
   first: boolean
   last: boolean
+  children?: ReactNode
 }
 
-function GatewayProfileGroup({ group, renderRows, onMove, first, last, onNewSessionSplit }: GatewayProfileGroupProps) {
+function GatewayProfileGroup({
+  group,
+  renderRows,
+  onMove,
+  first,
+  last,
+  onNewSessionSplit,
+  children
+}: GatewayProfileGroupProps) {
   const { t } = useI18n()
   const s = t.sidebar
   const copy = s.gatewayGroups
@@ -120,35 +179,42 @@ function GatewayProfileGroup({ group, renderRows, onMove, first, last, onNewSess
   }
 
   return (
-    <SidebarRowStack data-gateway-group={group.id} ref={sortable.ref} style={sortable.style}>
+    <SidebarRowStack
+      data-gateway-group={group.profile ? group.id : undefined}
+      data-gateway-section={!group.profile ? group.id : undefined}
+      ref={sortable.ref}
+      style={sortable.style}
+    >
       <SidebarGroupRow
         actions={
           <div className="flex items-center">
-            <WorkspaceAddButton
-              label={s.newSessionIn(label)}
-              onClick={startSession}
-              onPointerDown={
-                onNewSessionSplit
-                  ? event =>
-                      startNewSessionDrag(
-                        placement => {
-                          if (!open) {
-                            toggleGatewayGroup(group.id)
-                          }
+            {group.profile && (
+              <WorkspaceAddButton
+                label={s.newSessionIn(label)}
+                onClick={startSession}
+                onPointerDown={
+                  onNewSessionSplit
+                    ? event =>
+                        startNewSessionDrag(
+                          placement => {
+                            if (!open) {
+                              toggleGatewayGroup(group.id)
+                            }
 
-                          onNewSessionSplit(placement.dir, {
-                            anchor: placement.anchor,
-                            before: placement.before,
-                            profile: group.profile,
-                            route
-                          })
-                        },
-                        event,
-                        { label: s.newSessionIn(label), profile: group.profile, route }
-                      )
-                  : undefined
-              }
-            />
+                            onNewSessionSplit(placement.dir, {
+                              anchor: placement.anchor,
+                              before: placement.before,
+                              profile: group.profile,
+                              route
+                            })
+                          },
+                          event,
+                          { label: s.newSessionIn(label), profile: group.profile, route }
+                        )
+                    : undefined
+                }
+              />
+            )}
             <DropdownMenu>
               <DropdownMenuTrigger asChild>
                 <Button aria-label={`${copy.actions}: ${label}`} size="icon-xs" variant="ghost">
@@ -188,12 +254,16 @@ function GatewayProfileGroup({ group, renderRows, onMove, first, last, onNewSess
             dragging={sortable.dragging}
             dragHandleProps={sortable.dragHandleProps}
           >
-            <ProfileGlyph
-              className="size-full"
-              color={group.color ?? null}
-              isDefault={group.profile === 'default'}
-              name={group.profile!}
-            />
+            {group.profile ? (
+              <ProfileGlyph
+                className="size-full"
+                color={group.color ?? null}
+                isDefault={group.profile === 'default'}
+                name={group.profile}
+              />
+            ) : (
+              <Codicon name="remote" />
+            )}
           </SidebarRowGrab>
         }
         toggle={{ ariaLabel: s.projects.toggle(label, !open), onToggle: () => toggleGatewayGroup(group.id), open }}
@@ -201,6 +271,7 @@ function GatewayProfileGroup({ group, renderRows, onMove, first, last, onNewSess
       />
       {open && (
         <>
+          {children}
           {renderRows(sessions.slice(0, visibleCount))}
           {hiddenCount > 0 && (
             <WorkspaceShowMoreButton
diff --git a/website/docs/user-guide/multi-connection-desktop.md b/website/docs/user-guide/multi-connection-desktop.md
index d1d6977e0b..e8c3ddcafb 100644
--- a/website/docs/user-guide/multi-connection-desktop.md
+++ b/website/docs/user-guide/multi-connection-desktop.md
@@ -84,16 +84,19 @@ does not switch the current workspace.
 ## Organizing session groups
 
 In the Sessions sidebar's view menu, choose **Gateway & profile** while viewing
-all profiles. Each gateway/profile pair gets its own collapsible section, so two
-gateways with a `default` profile no longer share a section. Section labels start
-as the gateway name followed by the profile name.
+all profiles. Each gateway gets its own collapsible section, with profile
+subsections containing their sessions. Two gateways with a `default` profile
+stay separate. Gateway headers start with the saved connection name; profile
+headers show the profile name.
 
-Use a section's menu to **Rename group**, **Reset name**, **Move up**, or
+Use a gateway or profile section's menu to **Rename group**, **Reset name**, **Move up**, or
 **Move down**. Renaming changes only the sidebar label, not the gateway or profile.
+Gateways reorder as complete sections, and profiles reorder within their own gateway.
 Drag the section's leading icon to reorder it, or focus that handle and use
 Space, arrow keys, then Space to place it. Names, order, and collapsed sections
-are remembered on this desktop. The section's new-session action targets that
-section's gateway and profile.
+are remembered on this desktop. Collapsing a gateway preserves its profiles'
+individual collapse states. Each profile's new-session action targets that
+profile on its owning gateway.
 
 The Hermes Cloud panel also lists **Saved Cloud gateways** when portal discovery
 is signed out. **Use gateway** selects an existing saved connection without