Issues with drafts not decrypting when "left open" and is restarted (and passphrase not provided upon startup)

gpg_dude's Avatar


06 Jul, 2020 04:57 PM

I know there there has been a long history of issues with encrypting drafts and I've usually just considered it a sunk cost and done my own manual decrypt & copy/paste dance to work around them. But I wanted to reach out to see if there's a better/easier/more-reliable way to handle this since I just encountered the issue with 2 very long draft emails that are full of HTML & in-line image attachments which will be difficult, if not impossible to avoid having to re-create manually.

The behavior seems to be if I have encrypted drafts enable and leave one or more drafts open during a restart of When starts up, it prompts me for pinentry prior to showing me any of the application windows. This used to confuse me because I couldn't figure out what was even triggering GPG so I would often cancel in an over abundance of caution. However, if the reason for the prompt is to decrypt an encrypted draft like I believe happened in this case - then the drafts remain encrypted with the familiar attachments named encrypted.asc & Mail Attachment. While I can decrypt the file manually, I cannot just copy & paste the results back into a message as it is html. Even trying to use lynx --dump to convert it to plaintext leaves some cruft behind:

Content-Transfer-Encoding: quoted-printable Content-Type: text/html; charset=utf-8

Hi there, Responses = inline=E2=80=A6

and obviously loses all my formatting & embedded images.

Is there anyway to undo this or am I just going to have to piece them back together?

  1. Support Staff 1 Posted by Luke Le on 06 Jul, 2020 05:02 PM

    Luke Le's Avatar

    Yeah this one is unfortunately tough to handle right. We would probably have to close the window before Mail attempts to overwrite the draft, if you opt to not enter your passphrase right that moment.

    For now as a workaround, you can save the decrypted content as .eml file. Open that in Mail and press CMD + SHIFT + D. That should let you edit the email as a new draft.

    Please let us know if that helped.

  2. 2 Posted by gpg_dude on 06 Jul, 2020 09:34 PM

    gpg_dude's Avatar

    Yes, that did the trick. Thanks much. This might be a good one to add to the FAQ since there are so many support threads about it.

  3. Support Staff 3 Posted by Steve on 08 Jul, 2020 04:03 PM

    Steve's Avatar

    This is a bit of an edge case. We will discuss this but it happens fairly seldom as most users opt to store the OpenPGP password for their key in macOS keychain.

    If we receive more reports we will add this to the FAQ.

  4. Steve closed this discussion on 27 Jul, 2020 12:26 PM.

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