diff --git a/src/shared/release-channel.test.ts b/src/shared/release-channel.test.ts
index a2d66242d93..fb530d66347 100644
--- a/src/shared/release-channel.test.ts
+++ b/src/shared/release-channel.test.ts
@@ -324,4 +324,24 @@ describe('release channel', () => {
       '1.4.160-adhoc.20260728090000'
     ])
   })
+
+  it('sorts dev builds by their cut time across different base versions', () => {
+    const build = (version: string): ReleaseBuild => ({
+      tag: `v${version}`,
+      version,
+      channel: 'adhoc',
+      name: null,
+      publishedAt: null,
+      releaseUrl: `https://github.com/stablyai/orca-adhoc/releases/tag/v${version}`,
+      installerUrl: null
+    })
+    const sorted = sortReleaseBuildsNewestFirst([
+      build('1.4.207-adhoc.20260919025813'),
+      build('1.4.206-adhoc.20260919173504')
+    ])
+    expect(sorted.map((entry) => entry.version)).toEqual([
+      '1.4.206-adhoc.20260919173504',
+      '1.4.207-adhoc.20260919025813'
+    ])
+  })
 })
diff --git a/src/shared/release-channel.ts b/src/shared/release-channel.ts
index 056152ffcc9..7a7f3aa96b0 100644
--- a/src/shared/release-channel.ts
+++ b/src/shared/release-channel.ts
@@ -319,5 +319,28 @@ export type ReleaseBuild = {
 
 /** Newest first, so the picker's first row is always the channel's current tip. */
 export function sortReleaseBuildsNewestFirst(builds: ReleaseBuild[]): ReleaseBuild[] {
-  return [...builds].sort((left, right) => compareAppVersions(right.version, left.version))
+  return [...builds].sort((left, right) => {
+    // Dev build base versions can move backwards when a branch was cut before
+    // the latest main build. Their stamped build time, not semver, is the
+    // meaningful "newest" signal for the picker.
+    const leftStamp = parseDevBuildStamp(left.version)?.getTime() ?? null
+    const rightStamp = parseDevBuildStamp(right.version)?.getTime() ?? null
+    if (leftStamp !== null && rightStamp !== null && leftStamp !== rightStamp) {
+      return rightStamp - leftStamp
+    }
+
+    if (hasDedicatedReleaseRepo(left.channel) && hasDedicatedReleaseRepo(right.channel)) {
+      const leftPublished = left.publishedAt ? Date.parse(left.publishedAt) : Number.NaN
+      const rightPublished = right.publishedAt ? Date.parse(right.publishedAt) : Number.NaN
+      if (
+        Number.isFinite(leftPublished) &&
+        Number.isFinite(rightPublished) &&
+        leftPublished !== rightPublished
+      ) {
+        return rightPublished - leftPublished
+      }
+    }
+
+    return compareAppVersions(right.version, left.version)
+  })
 }