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September 11, 2026

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Bartleby asks for Accessibility now

If a tapback, a threaded reply, or a new conversation has failed with “Bartleby needs Accessibility access,” this is the fix. Bartleby never actually asked macOS for that permission. It checked, found it missing, and told you, without ever raising the dialog that grants it. Now it asks once, the first time you launch this build without it, the same way it asks for Contacts and Automation on a new Mac. Say yes and everything that goes through Messages works again: tapbacks, replies in a thread, starting a conversation, and downloading photos from iCloud.Said no, or closed the dialog? Settings → General → Accessibility shows whether it’s on, with an Ask Again button and a link straight to the System Settings pane. A failed tapback or reply now carries the same link, so you’re never told what’s wrong without a way to fix it.

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Also in this release

  • In group chats, reply threads now line up the way Messages draws them: the connecting line runs from the sender’s avatar rather than the bubble edge, the original message’s miniature shows a small avatar instead of a name, and a single reply no longer gets a “1 Reply” label.
  • Starting a new conversation with more than one person works the way it should. Picking someone you already have history with used to hide the recipient field and drop you into the message, which made adding a second person a fight. The field stays put, reads “Add another recipient,” and Tab still moves you to the message.
  • A new-conversation send that went through is no longer reported as failed. Bartleby now recognizes the message it just sent even when Messages stores it as styled text, or when more than one chat has the same people in it.
This entry was written by Claude Code and approved by Alex.
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September 11, 2026

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Archived means archived

Archived conversations no longer pop back into the inbox on their own. Four separate causes, all fixed: an archive could be undone by the next sync pass a few seconds later; by your own reply landing after you pressed E; by pressing E during the 5-second undo window; and by your own tapback landing after you archived. In every case Bartleby was treating something you did as new activity since you filed the conversation. Now only a message or reaction from someone else brings an archived conversation back. Thank you for the reports on this one.Threaded replies show the message they answer. Above a run of replies you’ll see a faded miniature of the original message, on its own side, with a “3 Replies” link under it that opens the thread for you to reply in. Click the miniature to jump to the original. Bringing the connecting line fully in step with Messages is next.Select several conversations with the keyboard. ⇧↓ and ⇧↑ extend the selection one row at a time, and ⌘A selects every conversation in view. Then E archives the whole set, and one Z brings it back.

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More in this release

  • Clicking anywhere in a conversation’s own space (not on a bubble) puts your cursor in the composer. If you step away for five minutes, focus returns to the conversation list so J and K work the moment you’re back.
  • Switching themes repaints every window at once.

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Bug fixes

  • A tapback that landed a beat late is no longer toggled back off by Bartleby’s retry.
  • The theme picker offers Adaptive and True Black; Flexoki is back in the workshop until it gets a full pass.

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Known issues

  • After switching themes, the Settings window can hold its previous background until you click in it.
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September 9, 2026

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I would prefer to tapback

You can now send tapbacks from Bartleby, including custom emoji. Right-click a message or press and hold to open the picker. Your reaction appears on the bubble while Bartleby confirms it in the background (this takes 1–2 seconds to send via iMessage). You can replace or remove your own reaction, and Apple’s Messages app should stay hidden throughout.Send Later finally has a working keyboard flow. Press ⌘⇧L, choose a time, and press Return in the composer to schedule. Scheduled messages appear in the transcript and leave the composer free for your next message. Right-click one to edit it, send it now, or delete it.
Important: keep Bartleby running on the Mac where you scheduled it so it can send!
Photos offloaded to iCloud now download for saved contacts when you open a conversation, with progress shown on each photo. Click a photo to move it to the front of the queue; if a download fails, click to retry. Messages with several photos now fetch each attachment.Finally, you can now archive conversations in bulk. Shift-click to select a range, ⌘-click to add or remove individual rows, then press E to archive the set. One Z brings the whole batch back. In ⌘K, “Archive Older Than…” offers six presets from 7 days to 1 year, or a duration you type, such as 45 days. Review the cutoff date and eligible count before confirming. Pinned conversations, drafts, staged attachments, scheduled sends, and snoozed conversations stay put when you archive by age.

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More in this release

  • Pinned conversations in Compact style have a thin bar in your system accent color. The freed indicator slot can show the snooze clock. Other pinned styles keep their pin icon. More improvements to this coming soon.
  • ⌘K finds conversations beyond the ones loaded in the inbox.
  • Settings → General has an optional email field for release updates. Your saved email syncs between Macs; subscribing works with or without usage reports turned on.
  • If you opt in, usage reporting run on launch and once a day while Bartleby is open. This helps me learn what is working for you and what is not, in addition to your excellent feedback (please keep it coming!). It includes the app version and build, macOS version, a random identifier for that Mac, the event type, and your email if you supplied one.
Usage analytics contain no message content or message counts. Your data remains securely within iMessage and never reaches Bartleby servers in any way.
  • If you like, you can turn off these automatic reports in Settings → General. Saving or clearing your email sends a separate registration update with the same fields. If you clear your email, it’s removed from our database permanently.

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Bug fixes

  • Fixed threaded replies failing to send.
  • Fixed typing digits or Space in Send Later losing input or focus.
  • Fixed the missing Dock badge. Settings → Alerts also lets you exclude reaction-only unreads from its count.
  • Incoming tapbacks now mark previously read conversations unread.
  • Link previews use the preview Messages already saved when available, reducing loading-related movement. Hidden preview files no longer appear as photo download placeholders.
  • The tapback picker opens above the message instead of covering its text.
  • Tab and ⇧Tab move between the recipient and message fields in Compose. Adding a recipient preserves your draft.
  • Settings opens centered over the Bartleby window. A stuck send no longer prevents quitting.
  • g g jumps to the top of the conversation. Clicking outside the photo viewer or contact card closes it; photo and control clicks keep their normal actions.
  • “Archive Older Than…” focuses its custom-duration field when it opens.
  • Archiving responds immediately to a leading E. Saving archive state stays fast as sync history grows.
  • Photos refresh when their downloads finish. Offloaded photos no longer leave failed thumbnail results stuck in the cache, and photo groups with missing message metadata now download correctly.
  • Bartleby opens its inbox after an update even when macOS cannot restore a window saved by the older build.
  • Editing a scheduled message preserves an existing draft and expands the composer to fit the restored text.
  • If your chosen send time passes while you are writing, Bartleby asks you to choose another time instead of sending immediately.
  • Scheduled sends keep their state across interruptions so a message with an uncertain result does not send again automatically.
  • A scheduled send that fails before anything leaves your Mac says so, keeps its time, and tries again when that time comes — including after a relaunch. Only a send that may have gone out is held for you to check first.
  • Send Later to someone you have never messaged is not available yet: Bartleby keeps your text and the chosen time and asks you to send now or schedule after the first message.
  • When a chosen send time has passed, the message tells you to clear the time or pick a new one.
  • Clicking a waiting photo keeps it at the front of the download queue even if you switch conversations and come back.
  • Upgrading takes a verified copy of your workflow database first, including on the oldest databases, and never removes the previous copy before the new one is safely written.

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Known issues

  • Photos in a conversation with an unsaved phone number do not download yet, and an occasional download can fail and need a retry.
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September 1, 2026

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Sync crash fix

0.4.0 crashed a few seconds after you switched sync on (oops). Fixed! Update both Macs to 0.4.1 before turning sync on; if you already turned it on in 0.4.0, your data is fine and it picks up where it left off.
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September 1, 2026

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Cross-device sync

Bartleby now syncs between Macs. Turn it on in Settings → Sync and each machine will sync what you’ve read, archived, snoozed, and pinned, along with lists, drafts, and settings. We’re using iCloud for sync so as long as you’re signed into the same iCloud account on both machines, it should work seamlessly.Before turning sync on:
  • Update both machines to 0.4.0 first. Then turn it on on your primary machine, let the sync populate, then turn it on for the other.
  • For now, messages you’ve scheduled to send later will send from the Mac that scheduled it to avoid duplicate sends; this means the machine with scheduled sends must be turned on during the scheduled time. In the future I’ll look into cloud solutions for this.
  • Draft text will sync, but attachments will not yet.

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Bug fixes

  • No more incorrect unread flags where you sent the last message. Tapbacks count as messages.
  • Composer will shrink back down after sending long messages.
  • Invisible ink messages hide again when you click a second time.
  • Location sharing in a one-on-one chat says the name of the person sharing, instead of “Someone.”
  • Conversations that once loaded empty could stay blank for good, this is fixed.
  • Bug reports sent from the app now render properly on the Canny feedback board (please keep reporting bugs!).
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August 31, 2026

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First in-app update

Proof of concept for in-app updates. Also the ? sheet now shows which version you’re running.
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August 31, 2026

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Easy app updates

Bartleby now updates itself! From this build on, you can update directly in the app via the Bartleby menu with the option to automatically download and install updates moving forward.
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August 31, 2026

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Ready for external testers

Bartleby is ready for external testing! With this version you can report a bug or request a feature without leaving the app: ⌘K, through the help menu, or from the ? sheet. Version and debugging details are shared automatically.

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Bug fixes

  • Reporting sheet owns keyboard focus and you can use Tab / ⇧+Tab to move between fields.
  • Composer now grows as you type.
  • No more empty space held for link previews that won’t load.
  • Onboarding copy fixes.
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August 29, 2026

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Lists, themes, and a build you can actually install

The first private alpha build of Bartleby. Bartleby reads the Messages history already on your Mac, adds the triage workflow Messages has never had, and sends through Messages itself.Triage without touching the mouse. J and K move, E archives, H snoozes, P pins, C composes, and Z undoes whatever you just did. Return drops you into the composer on whichever conversation is selected. ? shows the whole map, and ⌘K opens a command palette that searches every thread when what you typed isn’t a command. This should all feel familiar to power users of other similar tools.Lists, so the inbox is organized the way you think. Group people and conversations however you like, pin the lists to the left rail, and give each one its own icon.Snooze that actually wakes. A snoozed conversation comes back at the time you chose (or the next time they text you, if you choose).Awkward message types render correctly. Edited messages say they were edited. Shared locations appear as locations. Group events — people joining, leaving, renaming the thread — show up instead of silently vanishing. Tapbacks float the conversation and summarize in the preview the way Messages does, rather than arriving as their own message. Voice memos play in place. Invisible Ink stays hidden until you click it.

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More in this release

  • Themes, including a genuinely dark dark mode and Flexoki, plus five styles for pinned rows.
  • Screening filters behind their own button, Messages-style.
  • A contact panel that edits people and writes changes back to Contacts.
  • Window retains size and location between app opens.
  • Unknown numbers with unread texts get their own marker.
  • First build signed with Developer ID, notarized and stapled.