diff --git a/.changeset/config.json b/.changeset/config.json
index 0f83c3b95..c8468bd06 100644
--- a/.changeset/config.json
+++ b/.changeset/config.json
@@ -37,7 +37,7 @@
     ]
   ],
   "snapshot": {
-    "useCalculatedVersionForSnapshots": true,
+    "useCalculatedVersion": true,
     "prereleaseTemplate": "{tag}-{commit}"
   },
   "access": "public",
diff --git a/packages/cli/__tests__/lib/update-check.test.ts b/packages/cli/__tests__/lib/update-check.test.ts
index 4b160d426..889712372 100644
--- a/packages/cli/__tests__/lib/update-check.test.ts
+++ b/packages/cli/__tests__/lib/update-check.test.ts
@@ -84,6 +84,7 @@ import {
   maybeShowUpdateNotice,
   scheduleBackgroundRefresh,
   isVersionOutdated,
+  isOutdatedForChannel,
   resolveUpdateChannel,
   resolveInstallMethodOverride,
   isManualOnlyInstall,
@@ -115,6 +116,42 @@ describe("update-check", () => {
     mockGlobalConfig.value = null;
   });
 
+  // -----------------------------------------------------------------------
+  // isOutdatedForChannel
+  // -----------------------------------------------------------------------
+
+  describe("isOutdatedForChannel", () => {
+    it("treats any nightly dist-tag identity change as an update in both lexical directions", () => {
+      expect(isOutdatedForChannel("0.0.0-nightly-abc", "0.0.0-nightly-def", "nightly")).toBe(true);
+      expect(isOutdatedForChannel("0.0.0-nightly-def", "0.0.0-nightly-abc", "nightly")).toBe(true);
+      expect(
+        isOutdatedForChannel("0.0.0-nightly-f00d123", "0.0.0-nightly-0dead01", "nightly"),
+      ).toBe(true);
+    });
+
+    it("does not update nightly when the exact dist-tag version is already installed", () => {
+      expect(isOutdatedForChannel("0.0.0-nightly-abc", "0.0.0-nightly-abc", "nightly")).toBe(false);
+    });
+
+    it("uses semver for stable-to-nightly channel switches", () => {
+      expect(isOutdatedForChannel("0.7.0", "0.0.0-nightly-abc", "nightly")).toBe(false);
+      expect(isOutdatedForChannel("0.7.0", "0.8.0-nightly-abc", "nightly")).toBe(true);
+      expect(isOutdatedForChannel("0.8.0", "0.8.0-nightly-abc", "nightly")).toBe(false);
+    });
+
+    it("treats nightly-to-stable fallback on the nightly channel as an update when the dist-tag differs", () => {
+      // `fetchLatestVersion("nightly")` can fall back to `latest` if the
+      // nightly dist-tag is absent; prerelease-to-stable is a normal
+      // semver upgrade.
+      expect(isOutdatedForChannel("0.0.0-nightly-abc", "0.8.0", "nightly")).toBe(true);
+    });
+
+    it("keeps stable comparisons numeric instead of lexical", () => {
+      expect(isOutdatedForChannel("0.9.0", "0.10.0", "stable")).toBe(true);
+      expect(isOutdatedForChannel("0.7.0", "0.8.0", "stable")).toBe(true);
+    });
+  });
+
   // -----------------------------------------------------------------------
   // isVersionOutdated
   // -----------------------------------------------------------------------
@@ -1186,24 +1223,14 @@ describe("update-check", () => {
 
   describe("getUpdateCommand — channel-aware (Section B)", () => {
     it("uses @nightly tag for nightly channel", () => {
-      expect(getUpdateCommand("npm-global", "nightly")).toBe(
-        "npm install -g @aoagents/ao@nightly",
-      );
-      expect(getUpdateCommand("pnpm-global", "nightly")).toBe(
-        "pnpm add -g @aoagents/ao@nightly",
-      );
-      expect(getUpdateCommand("bun-global", "nightly")).toBe(
-        "bun add -g @aoagents/ao@nightly",
-      );
+      expect(getUpdateCommand("npm-global", "nightly")).toBe("npm install -g @aoagents/ao@nightly");
+      expect(getUpdateCommand("pnpm-global", "nightly")).toBe("pnpm add -g @aoagents/ao@nightly");
+      expect(getUpdateCommand("bun-global", "nightly")).toBe("bun add -g @aoagents/ao@nightly");
     });
 
     it("uses @latest tag for stable + manual channels", () => {
-      expect(getUpdateCommand("npm-global", "stable")).toBe(
-        "npm install -g @aoagents/ao@latest",
-      );
-      expect(getUpdateCommand("npm-global", "manual")).toBe(
-        "npm install -g @aoagents/ao@latest",
-      );
+      expect(getUpdateCommand("npm-global", "stable")).toBe("npm install -g @aoagents/ao@latest");
+      expect(getUpdateCommand("npm-global", "manual")).toBe("npm install -g @aoagents/ao@latest");
     });
 
     it("returns the brew upgrade notice for homebrew installs", () => {
diff --git a/packages/cli/src/lib/update-check.ts b/packages/cli/src/lib/update-check.ts
index 80ec8f586..7dc72019f 100644
--- a/packages/cli/src/lib/update-check.ts
+++ b/packages/cli/src/lib/update-check.ts
@@ -16,6 +16,7 @@ import { promisify } from "node:util";
 import {
   getInstalledAoVersion,
   getUpdateCheckCachePath,
+  isVersionOutdatedForChannel as coreIsVersionOutdatedForChannel,
   isVersionOutdated as coreIsVersionOutdated,
   loadGlobalConfig,
   type UpdateChannel,
@@ -181,8 +182,7 @@ export function classifyInstallPath(resolvedPath: string): InstallMethod {
     if (isPnpmGlobal) return "pnpm-global";
 
     const isNpmGlobal =
-      resolvedPath.includes("/lib/node_modules/") ||
-      resolvedPath.includes("\\lib\\node_modules\\");
+      resolvedPath.includes("/lib/node_modules/") || resolvedPath.includes("\\lib\\node_modules\\");
     if (isNpmGlobal) return "npm-global";
 
     return "unknown";
@@ -256,10 +256,7 @@ export function getGitUpdateRef(): string {
  * a notice so the user runs it themselves — auto-running `npm install -g`
  * inside a brew prefix overwrites brew's symlinks.
  */
-export function getUpdateCommand(
-  method: InstallMethod,
-  channel: UpdateChannel = "stable",
-): string {
+export function getUpdateCommand(method: InstallMethod, channel: UpdateChannel = "stable"): string {
   // "manual" channel maps to "stable" for the install command — the channel
   // affects when we check, not which tag manual installers should pick.
   const tag = channel === "nightly" ? "nightly" : "latest";
@@ -284,6 +281,14 @@ export function isManualOnlyInstall(method: InstallMethod): boolean {
   return method === "homebrew";
 }
 
+export function isOutdatedForChannel(
+  currentVersion: string,
+  latestVersion: string,
+  channel: UpdateChannel,
+): boolean {
+  return coreIsVersionOutdatedForChannel(currentVersion, latestVersion, channel);
+}
+
 // ---------------------------------------------------------------------------
 // Cache
 // ---------------------------------------------------------------------------
@@ -493,7 +498,7 @@ export async function checkForUpdate(opts?: {
         isOutdated:
           cached.installMethod === "git"
             ? cached.isOutdated === true
-            : isVersionOutdated(currentVersion, cached.latestVersion),
+            : isOutdatedForChannel(currentVersion, cached.latestVersion, channel),
         installMethod,
         recommendedCommand,
         checkedAt: cached.checkedAt,
@@ -540,14 +545,16 @@ export async function checkForUpdate(opts?: {
       currentVersionAtCheck: currentVersion,
       installMethod,
       channel,
-      isOutdated: isVersionOutdated(currentVersion, latestVersion),
+      isOutdated: isOutdatedForChannel(currentVersion, latestVersion, channel),
     });
   }
 
   return {
     currentVersion,
     latestVersion,
-    isOutdated: latestVersion ? isVersionOutdated(currentVersion, latestVersion) : false,
+    isOutdated: latestVersion
+      ? isOutdatedForChannel(currentVersion, latestVersion, channel)
+      : false,
     installMethod,
     recommendedCommand,
     checkedAt: latestVersion ? now : null,
@@ -585,7 +592,7 @@ export function maybeShowUpdateNotice(): void {
   const isOutdated =
     installMethod === "git"
       ? cached.isOutdated === true
-      : isVersionOutdated(currentVersion, cached.latestVersion);
+      : isOutdatedForChannel(currentVersion, cached.latestVersion, channel);
   if (!isOutdated) return;
 
   const channelSuffix = channel === "nightly" ? " (nightly)" : "";
diff --git a/packages/core/src/__tests__/version-compare.test.ts b/packages/core/src/__tests__/version-compare.test.ts
index 7eeedd9e4..859a49f32 100644
--- a/packages/core/src/__tests__/version-compare.test.ts
+++ b/packages/core/src/__tests__/version-compare.test.ts
@@ -1,12 +1,47 @@
 import { describe, it, expect } from "vitest";
 
-import { isVersionOutdated } from "../version-compare.js";
+import { isVersionOutdated, isVersionOutdatedForChannel } from "../version-compare.js";
 
 // Both `packages/cli/src/lib/update-check.ts` and
 // `packages/web/src/app/api/version/route.ts` import this implementation
 // from core. These tests are the single source of truth for the comparison
 // rules — if either consumer's behavior diverges, fix the consumer, not this.
 
+describe("isVersionOutdatedForChannel", () => {
+  it("treats nightly dist-tag changes as updates by identity in both lexical directions", () => {
+    expect(isVersionOutdatedForChannel("0.0.0-nightly-abc", "0.0.0-nightly-def", "nightly")).toBe(
+      true,
+    );
+    expect(isVersionOutdatedForChannel("0.0.0-nightly-def", "0.0.0-nightly-abc", "nightly")).toBe(
+      true,
+    );
+    expect(
+      isVersionOutdatedForChannel("0.0.0-nightly-f00d123", "0.0.0-nightly-0dead01", "nightly"),
+    ).toBe(true);
+  });
+
+  it("does not update nightly when the exact dist-tag version is already installed", () => {
+    expect(isVersionOutdatedForChannel("0.0.0-nightly-abc", "0.0.0-nightly-abc", "nightly")).toBe(
+      false,
+    );
+  });
+
+  it("uses semver for stable-to-nightly channel switches", () => {
+    expect(isVersionOutdatedForChannel("0.7.0", "0.0.0-nightly-abc", "nightly")).toBe(false);
+    expect(isVersionOutdatedForChannel("0.7.0", "0.8.0-nightly-abc", "nightly")).toBe(true);
+    expect(isVersionOutdatedForChannel("0.8.0", "0.8.0-nightly-abc", "nightly")).toBe(false);
+  });
+
+  it("treats nightly-to-stable fallback on the nightly channel as an update when the dist-tag differs", () => {
+    expect(isVersionOutdatedForChannel("0.0.0-nightly-abc", "0.8.0", "nightly")).toBe(true);
+  });
+
+  it("keeps stable comparisons numeric instead of lexical", () => {
+    expect(isVersionOutdatedForChannel("0.9.0", "0.10.0", "stable")).toBe(true);
+    expect(isVersionOutdatedForChannel("0.7.0", "0.8.0", "stable")).toBe(true);
+  });
+});
+
 describe("isVersionOutdated (shared core implementation)", () => {
   describe("numeric major/minor/patch", () => {
     it("treats lower major as older", () => {
diff --git a/packages/core/src/index.ts b/packages/core/src/index.ts
index a8a7f228e..5c5936c82 100644
--- a/packages/core/src/index.ts
+++ b/packages/core/src/index.ts
@@ -425,7 +425,7 @@ export { UpdateChannelSchema, InstallMethodOverrideSchema } from "./global-confi
 
 // Channel-aware semver comparison shared by the CLI's update-check and the
 // dashboard's /api/version route.
-export { isVersionOutdated } from "./version-compare.js";
+export { isVersionOutdated, isVersionOutdatedForChannel } from "./version-compare.js";
 
 // Cache-layer primitives for the update pipeline. Both the CLI and the
 // dashboard's /api/version route read the same cache file; centralising the
diff --git a/packages/core/src/version-compare.ts b/packages/core/src/version-compare.ts
index 224678656..a6145e16c 100644
--- a/packages/core/src/version-compare.ts
+++ b/packages/core/src/version-compare.ts
@@ -8,6 +8,34 @@
  * Spec: release-process.html §07 (Auto-update mechanics).
  */
 
+import type { UpdateChannel } from "./global-config.js";
+
+export function isVersionOutdatedForChannel(
+  current: string,
+  latest: string,
+  channel: UpdateChannel,
+): boolean {
+  if (channel === "nightly") {
+    const currentParsed = parseVersion(current);
+    const latestParsed = parseVersion(latest);
+    if (
+      isNightlyPrerelease(currentParsed.prerelease) &&
+      isNightlyPrerelease(latestParsed.prerelease)
+    ) {
+      return current !== latest;
+    }
+  }
+  return isVersionOutdated(current, latest);
+}
+
+function isNightlyPrerelease(prerelease: string | undefined): boolean {
+  return (
+    prerelease === "nightly" ||
+    prerelease?.startsWith("nightly-") === true ||
+    prerelease?.startsWith("nightly.") === true
+  );
+}
+
 /**
  * Returns true if `current` is an older version than `latest`.
  *
diff --git a/packages/web/src/app/api/version/route.ts b/packages/web/src/app/api/version/route.ts
index 768820ed8..2613a7d0a 100644
--- a/packages/web/src/app/api/version/route.ts
+++ b/packages/web/src/app/api/version/route.ts
@@ -13,7 +13,7 @@
 import { NextResponse } from "next/server";
 import {
   getInstalledAoVersion,
-  isVersionOutdated,
+  isVersionOutdatedForChannel,
   loadGlobalConfig,
   readUpdateCheckCacheRaw,
   type UpdateChannel,
@@ -53,7 +53,8 @@ export async function GET() {
   const latest = cache?.latestVersion && cacheMatchesChannel ? cache.latestVersion : null;
 
   // Git installs cache `latestVersion: "origin/main"` (a ref, not a semver),
-  // so `isVersionOutdated(current, "origin/main")` would always return false.
+  // so `isVersionOutdatedForChannel(current, "origin/main", channel)` would
+  // always return false.
   // The CLI works around this by trusting the precomputed `cached.isOutdated`
   // for git installs — mirror that here so the dashboard banner actually
   // appears when a git-installed user is behind origin/main.
@@ -62,7 +63,7 @@ export async function GET() {
     isOutdated =
       cache?.installMethod === "git"
         ? cache.isOutdated === true
-        : isVersionOutdated(current, latest);
+        : isVersionOutdatedForChannel(current, latest, channel);
   }
 
   const body: VersionResponse = {