diff --git a/packages/app/src/context/global-sync/event-reducer.test.ts b/packages/app/src/context/global-sync/event-reducer.test.ts
index 892129788e..c5bff2f157 100644
--- a/packages/app/src/context/global-sync/event-reducer.test.ts
+++ b/packages/app/src/context/global-sync/event-reducer.test.ts
@@ -249,8 +249,8 @@ describe("applyDirectoryEvent", () => {
   })
 
   test("cleans caches for trimmed sessions on session.created", () => {
-    const dropped = rootSession({ id: "ses_b" })
-    const kept = rootSession({ id: "ses_a" })
+    const dropped = rootSession({ id: "ses_a" })
+    const kept = rootSession({ id: "ses_b" })
     const message = userMessage("msg_1", dropped.id)
     const todos: string[] = []
     const [store, setStore] = createStore(
diff --git a/packages/app/src/context/global-sync/session-trim.ts b/packages/app/src/context/global-sync/session-trim.ts
index 800ba74a68..371fdc8198 100644
--- a/packages/app/src/context/global-sync/session-trim.ts
+++ b/packages/app/src/context/global-sync/session-trim.ts
@@ -10,7 +10,7 @@ export function compareSessionRecent(a: Session, b: Session) {
   const aUpdated = sessionUpdatedAt(a)
   const bUpdated = sessionUpdatedAt(b)
   if (aUpdated !== bUpdated) return bUpdated - aUpdated
-  return cmp(a.id, b.id)
+  return cmp(b.id, a.id)
 }
 
 export function takeRecentSessions(sessions: Session[], limit: number, cutoff: number) {
@@ -39,7 +39,7 @@ export function trimSessions(
   const all = input
     .filter((s) => !!s?.id)
     .filter((s) => !s.time?.archived)
-    .sort((a, b) => cmp(a.id, b.id))
+    .sort((a, b) => compareSessionRecent(a, b))
   const roots = all.filter((s) => !s.parentID)
   const children = all.filter((s) => !!s.parentID)
   const base = roots.slice(0, limit)
diff --git a/packages/app/src/pages/layout/helpers.ts b/packages/app/src/pages/layout/helpers.ts
index 48158debba..0cb73a77ac 100644
--- a/packages/app/src/pages/layout/helpers.ts
+++ b/packages/app/src/pages/layout/helpers.ts
@@ -21,7 +21,7 @@ function sortSessions(now: number) {
     const bUpdated = b.time.updated ?? b.time.created
     const aRecent = aUpdated > oneMinuteAgo
     const bRecent = bUpdated > oneMinuteAgo
-    if (aRecent && bRecent) return a.id < b.id ? -1 : a.id > b.id ? 1 : 0
+    if (aRecent && bRecent) return a.id > b.id ? -1 : a.id < b.id ? 1 : 0
     if (aRecent && !bRecent) return -1
     if (!aRecent && bRecent) return 1
     return bUpdated - aUpdated