diff --git a/ui/src/styles/chat/layout.css b/ui/src/styles/chat/layout.css
index 821ecbd3ab..3b330cacef 100644
--- a/ui/src/styles/chat/layout.css
+++ b/ui/src/styles/chat/layout.css
@@ -333,7 +333,7 @@
 
 .chat-controls__session {
   min-width: 140px;
-  max-width: 420px;
+  max-width: 300px;
 }
 
 .chat-controls__thinking {
@@ -400,7 +400,7 @@
 .chat-controls__session select {
   padding: 6px 10px;
   font-size: 13px;
-  max-width: 420px;
+  max-width: 300px;
   overflow: hidden;
   text-overflow: ellipsis;
 }
diff --git a/ui/src/ui/app-render.helpers.node.test.ts b/ui/src/ui/app-render.helpers.node.test.ts
index c386ccc0f7..ab6ba84396 100644
--- a/ui/src/ui/app-render.helpers.node.test.ts
+++ b/ui/src/ui/app-render.helpers.node.test.ts
@@ -1,6 +1,6 @@
 import { describe, expect, it } from "vitest";
 import type { SessionsListResult } from "./types.ts";
-import { resolveSessionDisplayName } from "./app-render.helpers.ts";
+import { parseSessionKey, resolveSessionDisplayName } from "./app-render.helpers.ts";
 
 type SessionRow = SessionsListResult["sessions"][number];
 
@@ -8,72 +8,238 @@ function row(overrides: Partial<SessionRow> & { key: string }): SessionRow {
   return { kind: "direct", updatedAt: 0, ...overrides };
 }
 
-describe("resolveSessionDisplayName", () => {
-  it("returns key when no row is provided", () => {
-    expect(resolveSessionDisplayName("agent:main:main")).toBe("agent:main:main");
+/* ================================================================
+ *  parseSessionKey – low-level key → type / fallback mapping
+ * ================================================================ */
+
+describe("parseSessionKey", () => {
+  it("identifies main session (bare 'main')", () => {
+    expect(parseSessionKey("main")).toEqual({ prefix: "", fallbackName: "Main Session" });
   });
 
-  it("returns key when row has no label or displayName", () => {
-    expect(resolveSessionDisplayName("agent:main:main", row({ key: "agent:main:main" }))).toBe(
-      "agent:main:main",
+  it("identifies main session (agent:main:main)", () => {
+    expect(parseSessionKey("agent:main:main")).toEqual({
+      prefix: "",
+      fallbackName: "Main Session",
+    });
+  });
+
+  it("identifies subagent sessions", () => {
+    expect(parseSessionKey("agent:main:subagent:18abfefe-1fa6-43cb-8ba8-ebdc9b43e253")).toEqual({
+      prefix: "Subagent:",
+      fallbackName: "Subagent:",
+    });
+  });
+
+  it("identifies cron sessions", () => {
+    expect(parseSessionKey("agent:main:cron:daily-briefing-uuid")).toEqual({
+      prefix: "Cron:",
+      fallbackName: "Cron Job:",
+    });
+  });
+
+  it("identifies direct chat with known channel", () => {
+    expect(parseSessionKey("agent:main:bluebubbles:direct:+19257864429")).toEqual({
+      prefix: "",
+      fallbackName: "iMessage · +19257864429",
+    });
+  });
+
+  it("identifies direct chat with telegram", () => {
+    expect(parseSessionKey("agent:main:telegram:direct:user123")).toEqual({
+      prefix: "",
+      fallbackName: "Telegram · user123",
+    });
+  });
+
+  it("identifies group chat with known channel", () => {
+    expect(parseSessionKey("agent:main:discord:group:guild-chan")).toEqual({
+      prefix: "",
+      fallbackName: "Discord Group",
+    });
+  });
+
+  it("capitalises unknown channels in direct/group patterns", () => {
+    expect(parseSessionKey("agent:main:mychannel:direct:user1")).toEqual({
+      prefix: "",
+      fallbackName: "Mychannel · user1",
+    });
+  });
+
+  it("identifies channel-prefixed legacy keys", () => {
+    expect(parseSessionKey("bluebubbles:g-agent-main-bluebubbles-direct-+19257864429")).toEqual({
+      prefix: "",
+      fallbackName: "iMessage Session",
+    });
+    expect(parseSessionKey("discord:123:456")).toEqual({
+      prefix: "",
+      fallbackName: "Discord Session",
+    });
+  });
+
+  it("handles bare channel name as key", () => {
+    expect(parseSessionKey("telegram")).toEqual({
+      prefix: "",
+      fallbackName: "Telegram Session",
+    });
+  });
+
+  it("returns raw key for unknown patterns", () => {
+    expect(parseSessionKey("something-unknown")).toEqual({
+      prefix: "",
+      fallbackName: "something-unknown",
+    });
+  });
+});
+
+/* ================================================================
+ *  resolveSessionDisplayName – full resolution with row data
+ * ================================================================ */
+
+describe("resolveSessionDisplayName", () => {
+  // ── Key-only fallbacks (no row) ──────────────────
+
+  it("returns 'Main Session' for agent:main:main key", () => {
+    expect(resolveSessionDisplayName("agent:main:main")).toBe("Main Session");
+  });
+
+  it("returns 'Main Session' for bare 'main' key", () => {
+    expect(resolveSessionDisplayName("main")).toBe("Main Session");
+  });
+
+  it("returns 'Subagent:' for subagent key without row", () => {
+    expect(resolveSessionDisplayName("agent:main:subagent:abc-123")).toBe("Subagent:");
+  });
+
+  it("returns 'Cron Job:' for cron key without row", () => {
+    expect(resolveSessionDisplayName("agent:main:cron:abc-123")).toBe("Cron Job:");
+  });
+
+  it("parses direct chat key with channel", () => {
+    expect(resolveSessionDisplayName("agent:main:bluebubbles:direct:+19257864429")).toBe(
+      "iMessage · +19257864429",
     );
   });
 
-  it("returns key when displayName matches key", () => {
+  it("parses channel-prefixed legacy key", () => {
+    expect(resolveSessionDisplayName("discord:123:456")).toBe("Discord Session");
+  });
+
+  it("returns raw key for unknown patterns", () => {
+    expect(resolveSessionDisplayName("something-custom")).toBe("something-custom");
+  });
+
+  // ── With row data (label / displayName) ──────────
+
+  it("returns parsed fallback when row has no label or displayName", () => {
+    expect(resolveSessionDisplayName("agent:main:main", row({ key: "agent:main:main" }))).toBe(
+      "Main Session",
+    );
+  });
+
+  it("returns parsed fallback when displayName matches key", () => {
     expect(resolveSessionDisplayName("mykey", row({ key: "mykey", displayName: "mykey" }))).toBe(
       "mykey",
     );
   });
 
-  it("returns key when label matches key", () => {
+  it("returns parsed fallback when label matches key", () => {
     expect(resolveSessionDisplayName("mykey", row({ key: "mykey", label: "mykey" }))).toBe("mykey");
   });
 
-  it("uses displayName prominently when available", () => {
-    expect(
-      resolveSessionDisplayName(
-        "discord:123:456",
-        row({ key: "discord:123:456", displayName: "My Chat" }),
-      ),
-    ).toBe("My Chat (discord:123:456)");
-  });
-
-  it("falls back to label when displayName is absent", () => {
+  it("uses label alone when available", () => {
     expect(
       resolveSessionDisplayName(
         "discord:123:456",
         row({ key: "discord:123:456", label: "General" }),
       ),
-    ).toBe("General (discord:123:456)");
+    ).toBe("General");
   });
 
-  it("prefers displayName over label when both are present", () => {
+  it("falls back to displayName when label is absent", () => {
+    expect(
+      resolveSessionDisplayName(
+        "discord:123:456",
+        row({ key: "discord:123:456", displayName: "My Chat" }),
+      ),
+    ).toBe("My Chat");
+  });
+
+  it("prefers label over displayName when both are present", () => {
     expect(
       resolveSessionDisplayName(
         "discord:123:456",
         row({ key: "discord:123:456", displayName: "My Chat", label: "General" }),
       ),
-    ).toBe("My Chat (discord:123:456)");
+    ).toBe("General");
   });
 
-  it("ignores whitespace-only displayName", () => {
+  it("ignores whitespace-only label and falls back to displayName", () => {
     expect(
       resolveSessionDisplayName(
         "discord:123:456",
-        row({ key: "discord:123:456", displayName: "   ", label: "General" }),
+        row({ key: "discord:123:456", displayName: "My Chat", label: "   " }),
       ),
-    ).toBe("General (discord:123:456)");
+    ).toBe("My Chat");
   });
 
-  it("ignores whitespace-only label", () => {
+  it("uses parsed fallback when whitespace-only label and no displayName", () => {
     expect(
       resolveSessionDisplayName("discord:123:456", row({ key: "discord:123:456", label: "   " })),
-    ).toBe("discord:123:456");
+    ).toBe("Discord Session");
   });
 
-  it("trims displayName and label", () => {
+  it("trims label and displayName", () => {
+    expect(resolveSessionDisplayName("k", row({ key: "k", label: "  General  " }))).toBe("General");
     expect(resolveSessionDisplayName("k", row({ key: "k", displayName: "  My Chat  " }))).toBe(
-      "My Chat (k)",
+      "My Chat",
     );
   });
+
+  // ── Type prefixes applied to labels / displayNames ──
+
+  it("prefixes subagent label with Subagent:", () => {
+    expect(
+      resolveSessionDisplayName(
+        "agent:main:subagent:abc-123",
+        row({ key: "agent:main:subagent:abc-123", label: "maintainer-v2" }),
+      ),
+    ).toBe("Subagent: maintainer-v2");
+  });
+
+  it("prefixes subagent displayName with Subagent:", () => {
+    expect(
+      resolveSessionDisplayName(
+        "agent:main:subagent:abc-123",
+        row({ key: "agent:main:subagent:abc-123", displayName: "Task Runner" }),
+      ),
+    ).toBe("Subagent: Task Runner");
+  });
+
+  it("prefixes cron label with Cron:", () => {
+    expect(
+      resolveSessionDisplayName(
+        "agent:main:cron:abc-123",
+        row({ key: "agent:main:cron:abc-123", label: "daily-briefing" }),
+      ),
+    ).toBe("Cron: daily-briefing");
+  });
+
+  it("prefixes cron displayName with Cron:", () => {
+    expect(
+      resolveSessionDisplayName(
+        "agent:main:cron:abc-123",
+        row({ key: "agent:main:cron:abc-123", displayName: "Nightly Sync" }),
+      ),
+    ).toBe("Cron: Nightly Sync");
+  });
+
+  it("does not prefix non-typed sessions with labels", () => {
+    expect(
+      resolveSessionDisplayName(
+        "agent:main:bluebubbles:direct:+19257864429",
+        row({ key: "agent:main:bluebubbles:direct:+19257864429", label: "Tyler" }),
+      ),
+    ).toBe("Tyler");
+  });
 });
diff --git a/ui/src/ui/app-render.helpers.ts b/ui/src/ui/app-render.helpers.ts
index a7e0b9aa2b..dcc8843bae 100644
--- a/ui/src/ui/app-render.helpers.ts
+++ b/ui/src/ui/app-render.helpers.ts
@@ -159,7 +159,7 @@ export function renderChatControls(state: AppViewState) {
             sessionOptions,
             (entry) => entry.key,
             (entry) =>
-              html`<option value=${entry.key}>
+              html`<option value=${entry.key} title=${entry.key}>
                 ${entry.displayName ?? entry.key}
               </option>`,
           )}
@@ -256,19 +256,96 @@ function resolveMainSessionKey(
   return null;
 }
 
+/* ── Channel display labels ────────────────────────────── */
+const CHANNEL_LABELS: Record<string, string> = {
+  bluebubbles: "iMessage",
+  telegram: "Telegram",
+  discord: "Discord",
+  signal: "Signal",
+  slack: "Slack",
+  whatsapp: "WhatsApp",
+  matrix: "Matrix",
+  email: "Email",
+  sms: "SMS",
+};
+
+const KNOWN_CHANNEL_KEYS = Object.keys(CHANNEL_LABELS);
+
+/** Parsed type / context extracted from a session key. */
+export type SessionKeyInfo = {
+  /** Prefix for typed sessions (Subagent:/Cron:). Empty for others. */
+  prefix: string;
+  /** Human-readable fallback when no label / displayName is available. */
+  fallbackName: string;
+};
+
+function capitalize(s: string): string {
+  return s.charAt(0).toUpperCase() + s.slice(1);
+}
+
+/**
+ * Parse a session key to extract type information and a human-readable
+ * fallback display name.  Exported for testing.
+ */
+export function parseSessionKey(key: string): SessionKeyInfo {
+  // ── Main session ─────────────────────────────────
+  if (key === "main" || key === "agent:main:main") {
+    return { prefix: "", fallbackName: "Main Session" };
+  }
+
+  // ── Subagent ─────────────────────────────────────
+  if (key.includes(":subagent:")) {
+    return { prefix: "Subagent:", fallbackName: "Subagent:" };
+  }
+
+  // ── Cron job ─────────────────────────────────────
+  if (key.includes(":cron:")) {
+    return { prefix: "Cron:", fallbackName: "Cron Job:" };
+  }
+
+  // ── Direct chat  (agent:<x>:<channel>:direct:<id>) ──
+  const directMatch = key.match(/^agent:[^:]+:([^:]+):direct:(.+)$/);
+  if (directMatch) {
+    const channel = directMatch[1];
+    const identifier = directMatch[2];
+    const channelLabel = CHANNEL_LABELS[channel] ?? capitalize(channel);
+    return { prefix: "", fallbackName: `${channelLabel} · ${identifier}` };
+  }
+
+  // ── Group chat  (agent:<x>:<channel>:group:<id>) ────
+  const groupMatch = key.match(/^agent:[^:]+:([^:]+):group:(.+)$/);
+  if (groupMatch) {
+    const channel = groupMatch[1];
+    const channelLabel = CHANNEL_LABELS[channel] ?? capitalize(channel);
+    return { prefix: "", fallbackName: `${channelLabel} Group` };
+  }
+
+  // ── Channel-prefixed legacy keys (e.g. "bluebubbles:g-…") ──
+  for (const ch of KNOWN_CHANNEL_KEYS) {
+    if (key === ch || key.startsWith(`${ch}:`)) {
+      return { prefix: "", fallbackName: `${CHANNEL_LABELS[ch]} Session` };
+    }
+  }
+
+  // ── Unknown — return key as-is ───────────────────
+  return { prefix: "", fallbackName: key };
+}
+
 export function resolveSessionDisplayName(
   key: string,
   row?: SessionsListResult["sessions"][number],
-) {
-  const displayName = row?.displayName?.trim() || "";
+): string {
   const label = row?.label?.trim() || "";
-  if (displayName && displayName !== key) {
-    return `${displayName} (${key})`;
-  }
+  const displayName = row?.displayName?.trim() || "";
+  const { prefix, fallbackName } = parseSessionKey(key);
+
   if (label && label !== key) {
-    return `${label} (${key})`;
+    return prefix ? `${prefix} ${label}` : label;
   }
-  return key;
+  if (displayName && displayName !== key) {
+    return prefix ? `${prefix} ${displayName}` : displayName;
+  }
+  return fallbackName;
 }
 
 function resolveSessionOptions(