diff --git a/packages/app/src/components/dialog-select-file.tsx b/packages/app/src/components/dialog-select-file.tsx
index 29a3666c034..4619d1765f5 100644
--- a/packages/app/src/components/dialog-select-file.tsx
+++ b/packages/app/src/components/dialog-select-file.tsx
@@ -15,6 +15,7 @@ import { useLayout } from "@/context/layout"
 import { useFile } from "@/context/file"
 import { useLanguage } from "@/context/language"
 import { decode64 } from "@/utils/base64"
+import { formatSessionTitle } from "@/utils/session-title"
 import { getRelativeTime } from "@/utils/time"
 
 type EntryType = "command" | "file" | "session"
@@ -206,7 +207,7 @@ function createSessionEntries(props: {
               .filter((s) => !!s?.id)
               .map((s) => ({
                 id: s.id,
-                title: s.title ?? props.language.t("command.session.new"),
+                title: formatSessionTitle(s.title ?? "") || props.language.t("command.session.new"),
                 description,
                 directory,
                 archived: s.time?.archived,
diff --git a/packages/app/src/pages/layout.tsx b/packages/app/src/pages/layout.tsx
index cb194052d1e..7c8c03455ea 100644
--- a/packages/app/src/pages/layout.tsx
+++ b/packages/app/src/pages/layout.tsx
@@ -18,6 +18,7 @@ import { useGlobalSync } from "@/context/global-sync"
 import { Persist, persisted } from "@/utils/persist"
 import { base64Encode } from "@opencode-ai/util/encode"
 import { decode64 } from "@/utils/base64"
+import { formatSessionTitle } from "@/utils/session-title"
 import { ResizeHandle } from "@opencode-ai/ui/resize-handle"
 import { Button } from "@opencode-ai/ui/button"
 import { Icon } from "@opencode-ai/ui/icon"
@@ -373,7 +374,7 @@ export default function Layout(props: ParentProps) {
         const session = store.session.find((s) => s.id === props.sessionID)
         const sessionKey = `${directory}:${props.sessionID}`
 
-        const sessionTitle = session?.title ?? language.t("command.session.new")
+        const sessionTitle = formatSessionTitle(session?.title ?? "") || language.t("command.session.new")
         const projectName = getFilename(directory)
         const description =
           e.details.type === "permission.asked"
diff --git a/packages/app/src/pages/layout/sidebar-items.tsx b/packages/app/src/pages/layout/sidebar-items.tsx
index 194f75f815b..68bc1017353 100644
--- a/packages/app/src/pages/layout/sidebar-items.tsx
+++ b/packages/app/src/pages/layout/sidebar-items.tsx
@@ -16,6 +16,7 @@ import { getFilename } from "@opencode-ai/util/path"
 import { type Message, type Session, type TextPart, type UserMessage } from "@opencode-ai/sdk/v2/client"
 import { For, Match, Show, Switch, createMemo, onCleanup, type Accessor, type JSX } from "solid-js"
 import { agentColor } from "@/utils/agent"
+import { formatSessionTitle } from "@/utils/session-title"
 
 const OPENCODE_PROJECT_ID = "4b0ea68d7af9a6031a7ffda7ad66e0cb83315750"
 
@@ -122,7 +123,7 @@ const SessionRow = (props: {
         </Switch>
       </div>
       <span class="text-14-regular text-text-strong grow-1 min-w-0 overflow-hidden text-ellipsis truncate">
-        {props.session.title}
+        {formatSessionTitle(props.session.title)}
       </span>
       <Show when={props.session.summary}>
         {(summary) => (
@@ -280,7 +281,7 @@ export const SessionItem = (props: SessionItemProps): JSX.Element => {
       <Show
         when={hoverEnabled()}
         fallback={
-          <Tooltip placement={props.mobile ? "bottom" : "right"} value={props.session.title} gutter={10}>
+          <Tooltip placement={props.mobile ? "bottom" : "right"} value={formatSessionTitle(props.session.title)} gutter={10}>
             {item}
           </Tooltip>
         }
diff --git a/packages/app/src/pages/session/message-timeline.tsx b/packages/app/src/pages/session/message-timeline.tsx
index b8410903550..4dded9bb2b6 100644
--- a/packages/app/src/pages/session/message-timeline.tsx
+++ b/packages/app/src/pages/session/message-timeline.tsx
@@ -12,6 +12,7 @@ import { ScrollView } from "@opencode-ai/ui/scroll-view"
 import type { UserMessage } from "@opencode-ai/sdk/v2"
 import { showToast } from "@opencode-ai/ui/toast"
 import { shouldMarkBoundaryGesture, normalizeWheelDelta } from "@/pages/session/message-gesture"
+import { formatSessionTitle } from "@/utils/session-title"
 import { SessionContextUsage } from "@/components/session-context-usage"
 import { useDialog } from "@opencode-ai/ui/context/dialog"
 import { useLanguage } from "@/context/language"
@@ -404,7 +405,7 @@ export function MessageTimeline(props: {
                           class="text-14-medium text-text-strong truncate grow-1 min-w-0 pl-2"
                           onDblClick={openTitleEditor}
                         >
-                          {titleValue()}
+                          {formatSessionTitle(titleValue() ?? "")}
                         </h1>
                       }
                     >
diff --git a/packages/app/src/utils/session-title.ts b/packages/app/src/utils/session-title.ts
new file mode 100644
index 00000000000..1c3f4277019
--- /dev/null
+++ b/packages/app/src/utils/session-title.ts
@@ -0,0 +1,9 @@
+export function formatSessionTitle(title: string): string {
+  const pipeIndex = title.indexOf("|")
+  if (pipeIndex === -1) return title
+  const group = title.slice(0, pipeIndex).trim()
+  const rest = title.slice(pipeIndex + 1).trim()
+  if (!group) return rest
+  const capitalized = group.charAt(0).toUpperCase() + group.slice(1)
+  return `${capitalized}: ${rest}`
+}
diff --git a/packages/opencode/src/cli/cmd/tui/component/dialog-session-list.tsx b/packages/opencode/src/cli/cmd/tui/component/dialog-session-list.tsx
index 775969bfcb3..23a9dff592e 100644
--- a/packages/opencode/src/cli/cmd/tui/component/dialog-session-list.tsx
+++ b/packages/opencode/src/cli/cmd/tui/component/dialog-session-list.tsx
@@ -34,29 +34,89 @@ export function DialogSessionList() {
 
   const sessions = createMemo(() => searchResults() ?? sync.data.session)
 
+  function parseSessionTitle(title: string): { group?: string; displayTitle: string } {
+    const pipeIndex = title.indexOf("|")
+    if (pipeIndex === -1) {
+      return { displayTitle: title }
+    }
+
+    const group = title.slice(0, pipeIndex).trim()
+    const displayTitle = title.slice(pipeIndex + 1).trim()
+
+    if (!group) {
+      return { displayTitle }
+    }
+
+    const capitalized = group.charAt(0).toUpperCase() + group.slice(1)
+    return { group: capitalized + ":", displayTitle }
+  }
+
   const options = createMemo(() => {
     const today = new Date().toDateString()
-    return sessions()
-      .filter((x) => x.parentID === undefined)
-      .toSorted((a, b) => b.time.updated - a.time.updated)
-      .map((x) => {
-        const date = new Date(x.time.updated)
-        let category = date.toDateString()
-        if (category === today) {
-          category = "Today"
-        }
-        const isDeleting = toDelete() === x.id
-        const status = sync.data.session_status?.[x.id]
-        const isWorking = status?.type === "busy"
-        return {
-          title: isDeleting ? `Press ${keybind.print("session_delete")} again to confirm` : x.title,
-          bg: isDeleting ? theme.error : undefined,
-          value: x.id,
-          category,
-          footer: Locale.time(x.time.updated),
-          gutter: isWorking ? <Spinner /> : undefined,
-        }
-      })
+    const allSessions = sessions().filter((x) => x.parentID === undefined)
+
+    // Separate into grouped and ungrouped
+    const grouped: typeof allSessions = []
+    const ungrouped: typeof allSessions = []
+
+    for (const session of allSessions) {
+      const parsed = parseSessionTitle(session.title)
+      if (parsed.group) {
+        grouped.push(session)
+      } else {
+        ungrouped.push(session)
+      }
+    }
+
+    // Sort grouped by group name ASC, then updated DESC
+    grouped.sort((a, b) => {
+      const aParsed = parseSessionTitle(a.title)
+      const bParsed = parseSessionTitle(b.title)
+      const groupCompare = (aParsed.group ?? "").localeCompare(bParsed.group ?? "")
+      if (groupCompare !== 0) return groupCompare
+      return b.time.updated - a.time.updated
+    })
+
+    // Sort ungrouped by updated DESC
+    ungrouped.sort((a, b) => b.time.updated - a.time.updated)
+
+    // Map grouped sessions
+    const groupedOptions = grouped.map((session) => {
+      const parsed = parseSessionTitle(session.title)
+      const isDeleting = toDelete() === session.id
+      const status = sync.data.session_status?.[session.id]
+      const isWorking = status?.type === "busy"
+      return {
+        title: isDeleting ? `Press ${keybind.print("session_delete")} again to confirm` : parsed.displayTitle,
+        bg: isDeleting ? theme.error : undefined,
+        value: session.id,
+        category: parsed.group,
+        footer: Locale.shortDateTime(session.time.updated),
+        gutter: isWorking ? <Spinner /> : undefined,
+      }
+    })
+
+    // Map ungrouped sessions
+    const ungroupedOptions = ungrouped.map((session) => {
+      const date = new Date(session.time.updated)
+      let category = date.toDateString()
+      if (category === today) {
+        category = "Today"
+      }
+      const isDeleting = toDelete() === session.id
+      const status = sync.data.session_status?.[session.id]
+      const isWorking = status?.type === "busy"
+      return {
+        title: isDeleting ? `Press ${keybind.print("session_delete")} again to confirm` : session.title,
+        bg: isDeleting ? theme.error : undefined,
+        value: session.id,
+        category,
+        footer: Locale.time(session.time.updated),
+        gutter: isWorking ? <Spinner /> : undefined,
+      }
+    })
+
+    return [...groupedOptions, ...ungroupedOptions]
   })
 
   onMount(() => {
diff --git a/packages/opencode/src/cli/cmd/tui/routes/session/header.tsx b/packages/opencode/src/cli/cmd/tui/routes/session/header.tsx
index 0c5ea9a8572..bbddc89b1ed 100644
--- a/packages/opencode/src/cli/cmd/tui/routes/session/header.tsx
+++ b/packages/opencode/src/cli/cmd/tui/routes/session/header.tsx
@@ -8,12 +8,17 @@ import type { AssistantMessage, Session } from "@opencode-ai/sdk/v2"
 import { useCommandDialog } from "@tui/component/dialog-command"
 import { useKeybind } from "../../context/keybind"
 import { useTerminalDimensions } from "@opentui/solid"
+import { formatSessionTitle, parseSessionTitleParts } from "@tui/util/session-title"
 
 const Title = (props: { session: Accessor<Session> }) => {
   const { theme } = useTheme()
+  const parts = createMemo(() => parseSessionTitleParts(props.session().title))
   return (
     <text fg={theme.text}>
-      <span style={{ bold: true }}>#</span> <span style={{ bold: true }}>{props.session().title}</span>
+      <span style={{ bold: true }}>#</span>{" "}
+      <Show when={parts().group} fallback={<span style={{ bold: true }}>{parts().rest}</span>}>
+        <span style={{ bold: true }}>{parts().group}</span> {parts().rest}
+      </Show>
     </text>
   )
 }
diff --git a/packages/opencode/src/cli/cmd/tui/routes/session/index.tsx b/packages/opencode/src/cli/cmd/tui/routes/session/index.tsx
index f20267e0820..5dc42a38843 100644
--- a/packages/opencode/src/cli/cmd/tui/routes/session/index.tsx
+++ b/packages/opencode/src/cli/cmd/tui/routes/session/index.tsx
@@ -58,6 +58,7 @@ import type { PromptInfo } from "../../component/prompt/history"
 import { DialogConfirm } from "@tui/ui/dialog-confirm"
 import { DialogTimeline } from "./dialog-timeline"
 import { DialogForkFromTimeline } from "./dialog-fork-from-timeline"
+import { formatSessionTitle } from "@tui/util/session-title"
 import { DialogSessionRename } from "../../component/dialog-session-rename"
 import { Sidebar } from "./sidebar"
 import { Flag } from "@/flag/flag"
@@ -231,7 +232,7 @@ export function Session() {
   const exit = useExit()
 
   createEffect(() => {
-    const title = Locale.truncate(session()?.title ?? "", 50)
+    const title = Locale.truncate(formatSessionTitle(session()?.title ?? ""), 50)
     const pad = (text: string) => text.padEnd(10, " ")
     const weak = (text: string) => UI.Style.TEXT_DIM + pad(text) + UI.Style.TEXT_NORMAL
     const logo = UI.logo("  ").split(/\r?\n/)
diff --git a/packages/opencode/src/cli/cmd/tui/routes/session/sidebar.tsx b/packages/opencode/src/cli/cmd/tui/routes/session/sidebar.tsx
index 42ac5fbe080..104f515779e 100644
--- a/packages/opencode/src/cli/cmd/tui/routes/session/sidebar.tsx
+++ b/packages/opencode/src/cli/cmd/tui/routes/session/sidebar.tsx
@@ -11,11 +11,13 @@ import { useKeybind } from "../../context/keybind"
 import { useDirectory } from "../../context/directory"
 import { useKV } from "../../context/kv"
 import { TodoItem } from "../../component/todo-item"
+import { formatSessionTitle, parseSessionTitleParts } from "@tui/util/session-title"
 
 export function Sidebar(props: { sessionID: string; overlay?: boolean }) {
   const sync = useSync()
   const { theme } = useTheme()
   const session = createMemo(() => sync.session.get(props.sessionID)!)
+  const titleParts = createMemo(() => parseSessionTitleParts(session().title))
   const diff = createMemo(() => sync.data.session_diff[props.sessionID] ?? [])
   const todo = createMemo(() => sync.data.todo[props.sessionID] ?? [])
   const messages = createMemo(() => sync.data.message[props.sessionID] ?? [])
@@ -92,7 +94,9 @@ export function Sidebar(props: { sessionID: string; overlay?: boolean }) {
           <box flexShrink={0} gap={1} paddingRight={1}>
             <box paddingRight={1}>
               <text fg={theme.text}>
-                <b>{session().title}</b>
+                <Show when={titleParts().group} fallback={<b>{titleParts().rest}</b>}>
+                  <b>{titleParts().group}</b> {titleParts().rest}
+                </Show>
               </text>
               <Show when={session().share?.url}>
                 <text fg={theme.textMuted}>{session().share!.url}</text>
diff --git a/packages/opencode/src/cli/cmd/tui/util/session-title.ts b/packages/opencode/src/cli/cmd/tui/util/session-title.ts
new file mode 100644
index 00000000000..6fea14ab908
--- /dev/null
+++ b/packages/opencode/src/cli/cmd/tui/util/session-title.ts
@@ -0,0 +1,19 @@
+export function formatSessionTitle(title: string): string {
+  const pipeIndex = title.indexOf("|")
+  if (pipeIndex === -1) return title
+  const group = title.slice(0, pipeIndex).trim()
+  const rest = title.slice(pipeIndex + 1).trim()
+  if (!group) return rest
+  const capitalized = group.charAt(0).toUpperCase() + group.slice(1)
+  return `${capitalized}: ${rest}`
+}
+
+export function parseSessionTitleParts(title: string): { group?: string; rest: string } {
+  const pipeIndex = title.indexOf("|")
+  if (pipeIndex === -1) return { rest: title }
+  const group = title.slice(0, pipeIndex).trim()
+  const rest = title.slice(pipeIndex + 1).trim()
+  if (!group) return { rest }
+  const capitalized = group.charAt(0).toUpperCase() + group.slice(1)
+  return { group: capitalized + ":", rest }
+}
diff --git a/packages/opencode/src/util/locale.ts b/packages/opencode/src/util/locale.ts
index 653da09a0b7..76e94dff164 100644
--- a/packages/opencode/src/util/locale.ts
+++ b/packages/opencode/src/util/locale.ts
@@ -28,6 +28,27 @@ export namespace Locale {
     }
   }
 
+  export function shortDateTime(input: number): string {
+    const date = new Date(input)
+    const now = new Date()
+    const isToday =
+      date.getFullYear() === now.getFullYear() &&
+      date.getMonth() === now.getMonth() &&
+      date.getDate() === now.getDate()
+
+    const timeStr = time(input)
+
+    if (isToday) {
+      return timeStr
+    } else {
+      const dateStr = date.toLocaleDateString(undefined, {
+        month: "short",
+        day: "numeric",
+      })
+      return `${dateStr} · ${timeStr}`
+    }
+  }
+
   export function number(num: number): string {
     if (num >= 1000000) {
       return (num / 1000000).toFixed(1) + "M"