StartTLS not available when sending email on gmail

Sync Issues
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#1

Description

Gmail has started to produce a "StartTLS is not available when trying to send a messsage in Gmail. Error occured in the middle of a conversation several hours ago where emails were going back and forth. One minute it worked…the next it didn’t. Emails sent directly from Gmail’s WEBUI send fine.

To Reproduce…

Steps to reproduce the behavior:

  1. Write email addressed to gmail user
    2.Click Send

Expected Behavior

Email is sent with no error.

Screenshots

image

[famewolf@HP810-135qe etc]$ openssl s_client -starttls imap -crlf -connect smtp.gmail.com:587
CONNECTED(00000003)

Setup

  • OS and Version: Manjaro KDE 20.1…1

    • Installation Method: aur/mailspring 1.8.0-1 (+163 6.07) (Installed)

  • Mailspring Version: 1.8.0-8983dca2

Additional Context

1637621 [2021-03-26 23:30:14.054] [metadata] [info] Metadata delta stream starting…
1637621 [2021-03-26 23:30:55.100] [background] [info] Syncing folder list…
1637621 [2021-03-26 23:30:55.242] [background] [info] syncFolderUIDRange for [Gmail]/All Mail, UIDs: 1 - 0, Heavy: false
1637621 [2021-03-26 23:31:22.679] [background] [info] - remote=140234, local=140235
1637621 [2021-03-26 23:31:23.112] [background] [info] Unlinking messages WHERE remoteFolderId = ? AND remoteUID IN (?) no longer present in remote range.
1637621 [2021-03-26 23:31:23.294] [background] [info] – 2 matches.
1637621 [2021-03-26 23:31:23.294] [background] [warning] [SLOW] Transaction=unlinkMessagesMatchingQuery > 80ms (181ms, 0 waiting to aquire)
1637621 [2021-03-26 23:31:23.678] [background] [info] syncFolderUIDRange for [Gmail]/Trash, UIDs: 1 - 0, Heavy: false
1637621 [2021-03-26 23:31:24.884] [background] [info] - remote=5013, local=5013
1637621 [2021-03-26 23:31:24.972] [background] [info] syncFolderUIDRange for [Gmail]/Spam, UIDs: 1 - 0, Heavy: false
1637621 [2021-03-26 23:31:25.204] [background] [info] - remote=381, local=381
1637621 [2021-03-26 23:31:25.209] [background] [info] Sync loop deleting unlinked messages with phase 1.
1637621 [2021-03-26 23:31:25.253] [background] [info] – Removing 2 unlinked messages
1637621 [2021-03-26 23:31:25.253] [background] [info] – Removing “StartTLS not available” (PhX6bJ6h3ZNqjUrNn64DshTwLCpLWd1LyS1gJGJ8s)
1637621 [2021-03-26 23:31:25.254] [background] [info] – Removing “StartTLS not available” (VkimkTP2LFuFd7TkyMfzPkFcGAyGMsbhaP9WKN1PR)
1637621 [2021-03-26 23:31:25.268] [background] [info] Sync loop complete.
1637621 [2021-03-26 23:33:25.268] [background] [info] Syncing folder list…
1637621 [2021-03-26 23:33:25.414] [background] [info] syncFolderUIDRange for [Gmail]/All Mail, UIDs: 576861 - 577303, Heavy: false
1637621 [2021-03-26 23:33:26.192] [background] [info] - remote=400, local=400
1637621 [2021-03-26 23:33:26.550] [background] [info] syncFolderUIDRange for [Gmail]/Trash, UIDs: 319559 - 328473, Heavy: false
1637621 [2021-03-26 23:33:26.833] [background] [info] - remote=400, local=400
1637621 [2021-03-26 23:33:26.905] [background] [info] syncFolderUIDRange for [Gmail]/Spam, UIDs: 1 - 14919, Heavy: false
1637621 [2021-03-26 23:33:27.145] [background] [info] - remote=381, local=381
1637621 [2021-03-26 23:33:27.147] [background] [info] Sync loop deleting unlinked messages with phase 2.
1637621 [2021-03-26 23:33:27.186] [background] [info] Sync loop complete.

Bundle: Compatibility
#2

This happens to me too, but if I restart my computer it works. Maybe this is a clue to what’s wrong?

#3

Has been regularly happening to me for the past 2-3 months too - especially when I leave Mailspring running for longer periods of time (overnight is usually enough).

Restarting Mailspring (not the computer) clears the problem and I can re-send the e-mail from draft afterwards.

Mailspring snap on Ubuntu 20.10
mailspring 1.8.0 498 latest/stable foundry376✓ -

#4

I’m also on linux but using the compiled version on Manjaro. It’s not happening to Aquamail on my phone so I know it’s not a “third party email client” issue with gmail. Seem’s specific to Mailspring and popped up after months of working on the SAME version. I also tried the 1.8.1 Mailspring Libre with identical results/issues. It’s happening often enough that I’ve started opening the webui again and have considered abandoning mailspring.

#5

Linux is not windows. The only time you should HAVE to reboot linux is when upgrading kernels. I’ve had mine going for weeks without reboots.

#6

Mailspring runs in the background when the app is closed. Rather than figuring out which processes to kill, I restarted the computer. Then it worked. It’s a Mailspring problem.

#7

this has started happening to me as well … haven’t been able to send mail from mailspring for 2 days now … run ubuntu 18.04 …

so killing mailspring is the solution?

I guess I’ll give it a go … but this is pretty annoying

#8

killing mailspring process has worked …