I see the attached ErrorSendMessage every 2-3 emails I send at the moment. Just started happening the other day.
If I hit re-send enough times, it will finally send. Does anybody else see this or know how to fix it? Driving me up the wall and, at times making mailspring useless to me.
Intermittent send failures like this are almost always SMTP connection reliability issues rather than a Mailspring bug — the connection to the SMTP server drops or times out mid-send, and the retry usually succeeds because a fresh connection is established. A few things worth checking:
If you’re on a VPN or behind a corporate firewall, the connection may be getting interrupted.
Check your SMTP security settings (Preferences → Accounts → your account) — if your server supports STARTTLS on port 587, that can sometimes be more stable than SSL/TLS on 465.
Logs are in ~/.config/Mailspring/logs/ (Linux) or ~/Library/Application Support/Mailspring/logs/ (macOS) — searching for “ErrorSendMessage” there will show the underlying error, which helps diagnose the root cause.