diff --git a/apps/desktop/src/app/session/hooks/use-session-list-actions.ts b/apps/desktop/src/app/session/hooks/use-session-list-actions.ts
index d7ab9ea0914c0..596a336f4e316 100644
--- a/apps/desktop/src/app/session/hooks/use-session-list-actions.ts
+++ b/apps/desktop/src/app/session/hooks/use-session-list-actions.ts
@@ -262,8 +262,12 @@ export function useSessionListActions({ profileScope }: UseSessionListActionsArg
       ...mergeSessionPage(prev.filter(inKey), result.sessions, keep)
     ])
 
-    // A full window back means the profile still has more on disk.
-    const truncated = result.sessions.length >= loaded + SIDEBAR_SESSIONS_PAGE_SIZE
+    // A full window back means the profile still has more on disk — but pinned
+    // rows arrive as a back-fill PAST the limit, so counting them fakes a full
+    // page and the "Load more" never goes away (it re-fetches the same rows
+    // forever). Only unpinned rows count toward the window.
+    const unpinned = result.sessions.filter(s => !s.pinned).length
+    const truncated = unpinned >= loaded + SIDEBAR_SESSIONS_PAGE_SIZE
     setSessionProfilesTruncated(prev => ({ ...prev, [key]: truncated }))
   }, [])
 
diff --git a/apps/desktop/src/hermes.ts b/apps/desktop/src/hermes.ts
index f33d05226c106..b931fe8678f5e 100644
--- a/apps/desktop/src/hermes.ts
+++ b/apps/desktop/src/hermes.ts
@@ -370,6 +370,26 @@ export function pluginSocket(pluginId: string, path: string, onMessage: (data: u
   }
 }
 
+/**
+ * Trim a page to its window WITHOUT discarding pinned rows.
+ *
+ * The list endpoints deliberately back-fill pinned conversations past their
+ * LIMIT — a pin means "always reachable", so an aged-out pinned chat is
+ * appended after the recency window. A plain `slice(0, limit)` throws exactly
+ * those rows away again, which is why pins silently stopped rendering past
+ * some count: the sidebar could only ever show the pins that happened to fall
+ * inside the most-recent page.
+ */
+function pageWindow(sessions: SessionInfo[], limit: number): SessionInfo[] {
+  if (sessions.length <= limit) {
+    return sessions
+  }
+
+  const recent = sessions.slice(0, limit)
+
+  return [...recent, ...sessions.slice(limit).filter(session => session.pinned)]
+}
+
 export async function listSessions(
   limit = 40,
   minMessages = 0,
@@ -385,7 +405,7 @@ export async function listSessions(
 
   return {
     ...result,
-    sessions: result.sessions.slice(0, limit),
+    sessions: pageWindow(result.sessions, limit),
     offset: 0
   }
 }
@@ -426,7 +446,7 @@ export async function listAllProfileSessions(
 
   return {
     ...result,
-    sessions: result.sessions.slice(0, limit),
+    sessions: pageWindow(result.sessions, limit),
     offset: 0
   }
 }
@@ -445,14 +465,16 @@ export interface SidebarSessionSlice {
 
 /** Which profiles filled their per-profile window in a returned page. The
  *  legacy per-slice endpoint doesn't report this, so derive it from the rows:
- *  a profile at (or over) the cap still has more on disk. */
+ *  a profile at (or over) the cap still has more on disk. Pinned rows are
+ *  discounted — they're back-filled past the LIMIT, so counting them fakes a
+ *  full page and leaves a "Load more" that can never resolve. */
 function profilesTruncatedFrom(sessions: SessionInfo[], cap: number): Record<string, boolean> {
   const counts = new Map<string, number>()
 
   for (const session of sessions) {
     const key = session.profile || 'default'
 
-    counts.set(key, (counts.get(key) ?? 0) + 1)
+    counts.set(key, (counts.get(key) ?? 0) + (session.pinned ? 0 : 1))
   }
 
   return Object.fromEntries([...counts].map(([name, count]) => [name, count >= cap]))