Documents stay in the conversation, and retries keep your work

Ask about the document you shared

An attached PDF could appear in the conversation while Bobby had too little of its text to answer your next question. Permitted excerpts now reach Bobby with the attachment context and remain available for follow-ups. You can ask about the details in a travel document, then use those details with the existing trip tools.

New scanned PDFs now get local text recognition (OCR), including documents whose pages are readable images. Ridgeback keeps any existing text and attempts to read up to 20 scanned pages within a time limit. It reports incomplete extraction when it cannot finish.

Bobby still receives a limited saved excerpt, so a detail elsewhere in the PDF may be unavailable. Previously uploaded files keep their saved extraction; uploading identical bytes again does not refresh it.

Android gives document processing enough time to finish before treating an upload as failed. Desktop uploads also keep the original filename, so Bobby can find an attachment by the name you use.

Documents in private conversations stay behind that conversation’s access checks. Their download links follow those checks, and documents stay out of the shared photo library.

Keep typing when the keyboard opens

On Android, the message box stays above the keyboard. Navigation tabs hide while you type to leave room on smaller screens, and return when you close the keyboard. The fix also protects the typing area when a document is attached.

A failed send leaves your next draft alone

Sometimes a message reaches the server but its reply never reaches your phone. On iPhone, Android, and the desktop apps, retrying that same message now preserves its identity and attachments, so a lost response does not turn the retry into a second request for Bobby to act on.

On iPhone and Android, text or an attachment you add while a send is pending survives a failure. The failed message stays available to retry without replacing the new draft.

Signing out also cancels the authority of an earlier sign-in refresh. A late response can no longer restore the account you left or clear a different account you have since signed into.

Undo respects later edits

Undo now checks and reverses an action together, so an edit made by someone else cannot slip between those steps and disappear. If a later change conflicts with the reversal, the undo is refused and the later work remains.

Adding someone to a trip again, or attaching a list that is already there, no longer creates an undo that removes the existing relationship. When household members share a name, Bobby asks which person you mean.

A used storage destination stays in place

Once uploads or other stored records use a destination, Ridgeback blocks switching buckets or disconnecting it. This keeps existing files and outstanding cleanup tied to the bucket that holds them, including while an upload is starting. The same protection applies when files already use Ridgeback’s storage and you try to move to your own bucket.

You can still rotate credentials for the same destination once the new credentials pass verification. Deleting photos does not unlock a bucket change: upload history still matters. There is no storage migration tool yet, and this release does not relocate files left in an older destination.

The photo library also reaches photos without a capture date when you page through it, including when several photos share the same timestamps.

Get the build

iPhone builds arrive through TestFlight. Android, macOS and Linux downloads are on the home page.