Switching From Canary Mail Without Losing Encrypted Mail

If you're looking up how to switch from Canary Mail to another email client, the good news is that almost all of it is a routine IMAP reconnect. Your folders, your labels, and every message you've ever received live on your mail provider's server, not inside Canary — point a new app at the same account and they're already there.

The one piece that doesn't move by itself is anything encrypted. PGP messages and SecureSend links depend on a private key or a hosted reader tied to Canary, not to the mailbox underneath it. Get that part right before you cancel, and the rest of this move takes an afternoon.

What actually moves when you switch — and what doesn't#

Canary Mail is an IMAP client wrapped around accounts you already have — Gmail, Outlook, iCloud, Yahoo, Proton Mail, Zoho, Exchange, or plain IMAP. Canary doesn't host your mail; your provider does. So the messages, the folder structure, and the read state of every conversation live on the mail server, regardless of which app is pointed at it.

What Canary holds locally is everything built on top of that protocol: your PGP key pair, if it generated one rather than importing a key you already had; SecureSend's hosted-reader configuration; the AI Copilot's on-device model; and any rules, signatures, or contact profiles you've saved. None of that lives on the server, so none of it arrives automatically in whatever you switch to.

• Moves automatically — every message, folder, label, and read/unread flag, because your provider owns them, not Canary.
• Moves only if you export it first — your PGP private key, if Canary generated it rather than importing one you already had elsewhere.
• Doesn't move at all — Canary's AI Copilot history, its prioritization model, and any saved rules, signatures, or contact profiles. These get rebuilt in the new client, not transferred.
• Needs a decision, not an export — any SecureSend link you've already sent. It lives on Canary's hosted reader, independent of which client you use going forward.

Pre-migration checklist#

Do these before you touch your account settings, not after. Every item here is either impossible or genuinely painful to redo once Canary can no longer reach your accounts.

• Find out where your PGP key came from. If you imported it from GPG Suite, Keychain, or another OpenPGP tool before connecting Canary, it already lives outside the app and there's nothing to export.
• List every account connected to Canary, including ones added years ago and forgotten — its unlimited-account allowance on paid tiers is exactly why people accumulate mailboxes inside one app.
• Note which SecureSend messages you might still need. The sent copy stays visible inside Canary until you cancel, so check it while you still can.
• Back up any locally saved templates, signatures, or rules as plain text — Canary doesn't publish a bulk-export format for them.
• Confirm your target client actually supports OpenPGP if encryption matters. Not every mail app handles it natively; some need a plugin, others manage encrypted mail through their own, non-PGP system entirely.

How to switch from Canary Mail to another email client, step by step#

1. 1

   Export your PGP key pair from Canary

   Canary's own security documentation describes PGP as OpenPGP-compatible, with key management available to people who want direct control over it rather than leaving it fully automatic. Use that access to export both the public and private halves as a standard key file before you disconnect the account.

2. 2

   Add the same account to the new client over IMAP

   Connect the Gmail, Outlook, iCloud, or IMAP account you're moving through the new app's normal setup flow. This doesn't touch or risk the account you're leaving, so run it with Canary still installed.

3. 3

   Import the key pair into the new client

   Most desktop apps that support OpenPGP — through GPG Suite, Mailvelope, Thunderbird's built-in support, or native handling — import a standard key file the same way. Once it's in, PGP mail already sitting in your inbox decrypts immediately, because the message and the key are two separate things and the message never depended on Canary to exist.

4. 4

   Let the initial sync finish before you judge anything

   A large mailbox can take from minutes to several hours to index in a new app. Judge search, threading, and folder structure only once the sync reports done — a partial index looks broken and usually isn't.

5. 5

   Recreate rules, signatures, and templates by hand

   These live in Canary's local settings, not on the mail server, so there's no export-import path for them. Budget twenty minutes for a typical setup — most people have fewer saved rules than they remember having.

6. 6

   Decide what to do about outstanding SecureSend links

   Messages you already sent through SecureSend live on Canary's hosted reader, not in your mailbox, so switching clients doesn't delete or break them for the recipient. If your new client has no equivalent, tell people ahead of your next sensitive email rather than letting them discover it's gone.

7. 7

   Cancel Canary only after you've confirmed decryption works

   Send yourself a test PGP message under the new setup and confirm it decrypts before the subscription lapses. This costs nothing and catches a key-export mistake while it's still fixable.

What breaks when you leave Canary Mail#

Most of what people worry about turns out to be fine — mail, folders, and labels all survive the move without you doing anything. The list of things that genuinely need a workaround is short, and two of them are worth taking seriously before you cancel.

Rollback plan: how to back out without losing anything#

Don't cancel Canary the same day you switch. Keep the subscription active until the new client has handled a real week of your mail — including whatever you use PGP for.

• Don't delete your PGP key pair from Canary until you've confirmed it imports and decrypts correctly elsewhere. Deleting the only copy of a private key isn't reversible.
• If a rule or automated reply you relied on turns out to matter more than expected, Canary is still there to fall back to while you rebuild the equivalent.
• If the new client's setup goes wrong halfway through — a stuck sync, a rejected permission grant — your mail on the provider's server is untouched, and Canary keeps working exactly as it did before you started.

Doing the switch without any downtime#

You don't have to pick a day to be without email. IMAP is a protocol both apps can read against at once, so connecting a second client doesn't put the first one at risk.

• Run both apps side by side for a week. Gmail, Outlook, and any real IMAP provider expect multiple simultaneous connections — that's normal use, not a workaround.
• Keep reading in Canary until you trust the new client's drafts and signatures, then start replying from there instead.
• Migrate one account first if several are connected to Canary. Confirm the whole flow — PGP included, if that account uses it — before repeating it on the rest.
• Turn on notifications in only one app at a time once you're confident, so you're not triaging the same message twice.

Where AI Emaily fits#

If part of why you're leaving is that Canary's AI stayed at the writing desk — drafting and summarizing, never touching triage, filing, or follow-ups — that's a different gap than PGP support, and worth naming plainly. We build AI Emaily, an AI-native client that runs the same Gmail, Outlook, and IMAP accounts you're moving here, side by side.

In Copilot mode, nothing sends without your approval, and every action the agent takes is reversible and written to an audit log you can read line by line. Its voice comes from a Personal Context brain and per-client profiles you set, not from scraping your sent mail.

State the limit too: we don't ship PGP or a SecureSend-style secure reader, so if encrypted delivery to non-technical recipients is why you're here, that requirement belongs to whichever client replaces Canary on that dimension. AI Emaily is a 7-day free trial on Pro and Autopilot — card required, $0 if you cancel before day seven.