# Sendemail fail with VPN **URL:** \ **Category:** Support\ **Created:** [June 2, 2026, 12:59pm UTC](https://forum.duplicati.com/t/sendemail-fail-with-vpn/22445 "2026-06-02T12:59:29Z")\ **Posts on this page:** 9\ **Page:** 1
**Author:** ![scrognoid](https://forum.duplicati.com/letter_avatar_proxy/v4/letter/s/c4cdca/32.png) [@scrognoid](https://forum.duplicati.com/u/scrognoid)\ **Post date:** [June 2, 2026, 12:59pm UTC](https://forum.duplicati.com/t/sendemail-fail-with-vpn/22445/1 "2026-06-02T12:59:29Z")
Duplicati has never been able to send email when VPN is on. Is there a fix for this? ---
**Author:** ![f1assistance](https://forum.duplicati.com/user_avatar/forum.duplicati.com/f1assistance/32/11553_2.png) [@f1assistance](https://forum.duplicati.com/u/f1assistance)\ **Post date:** [June 2, 2026, 1:06pm UTC](https://forum.duplicati.com/t/sendemail-fail-with-vpn/22445/2 "2026-06-02T13:06:54Z")
Which email service and VPN are you using? ---
**Author:** ![ts678](https://forum.duplicati.com/letter_avatar_proxy/v4/letter/t/8491ac/32.png) [@ts678](https://forum.duplicati.com/u/ts678)\ **Post date:** [June 2, 2026, 3:12pm UTC](https://forum.duplicati.com/t/sendemail-fail-with-vpn/22445/3 "2026-06-02T15:12:55Z")
Does fail make any warning or error? Check for red icons in bottom right. [The SEND-MAIL command](https://docs.duplicati.com/community-docs/community-docs-using-duplicati-from-the-commandline#the-send-mail-command) (citing the old docs) can be useful for testing. I think a mail send logs details at `profiling` log level if you want to see. About Duplicati → Logs → Live is one way to see that. You can also use: `console-log-level=profiling` if you wind up running in Commandline. ---
**Author:** ![scrognoid](https://forum.duplicati.com/letter_avatar_proxy/v4/letter/s/c4cdca/32.png) [@scrognoid](https://forum.duplicati.com/u/scrognoid)\ **Post date:** [June 2, 2026, 7:52pm UTC](https://forum.duplicati.com/t/sendemail-fail-with-vpn/22445/4 "2026-06-02T19:52:37Z")
I use PIA VPN. Thunderbird has no trouble sending email behind it. Duplicati use send **e** mail command, last I checked. Also note, I running Linux Mint 21.3. > Warning while running 2018jennifer\_MSOD > 2026-06-02 15:43:51 -04 - [Warning-Duplicati.Library.Modules.Builtin.ReportHelper-ReportSubmitError]: Failed to send message: System.TimeoutException: The operation has timed out. TimeoutException: The operation has timed out. ---
**Author:** ![f1assistance](https://forum.duplicati.com/user_avatar/forum.duplicati.com/f1assistance/32/11553_2.png) [@f1assistance](https://forum.duplicati.com/u/f1assistance)\ **Post date:** [June 2, 2026, 10:46pm UTC](https://forum.duplicati.com/t/sendemail-fail-with-vpn/22445/5 "2026-06-02T22:46:17Z")
Does Duplicati send an email when the VPN is disabled? ---
**Author:** ![scrognoid](https://forum.duplicati.com/letter_avatar_proxy/v4/letter/s/c4cdca/32.png) [@scrognoid](https://forum.duplicati.com/u/scrognoid)\ **Post date:** [June 3, 2026, 12:28am UTC](https://forum.duplicati.com/t/sendemail-fail-with-vpn/22445/6 "2026-06-03T00:28:02Z")
Yes, I does work when VPN is off ---
**Author:** ![scrognoid](https://forum.duplicati.com/letter_avatar_proxy/v4/letter/s/c4cdca/32.png) [@scrognoid](https://forum.duplicati.com/u/scrognoid)\ **Post date:** [June 3, 2026, 1:26am UTC](https://forum.duplicati.com/t/sendemail-fail-with-vpn/22445/7 "2026-06-03T01:26:56Z")
Just did a test to make sure it was not VPN server specific. It is not. Fails with in-country server as well. ---
**Author:** ![ts678](https://forum.duplicati.com/letter_avatar_proxy/v4/letter/t/8491ac/32.png) [@ts678](https://forum.duplicati.com/u/ts678)\ **Post date:** [June 4, 2026, 9:33pm UTC](https://forum.duplicati.com/t/sendemail-fail-with-vpn/22445/8 "2026-06-04T21:33:19Z")
> [@scrognoid](#): > > Duplicati use send **e** mail command, last I checked. Please show what you found when you checked. I haven’t heard of such a thing. There is no such string in [docs.duplicati.com](http://docs.duplicati.com), [prev-docs.duplicati.com](http://prev-docs.duplicati.com), or [source](https://github.com/duplicati/duplicati). There is a [sendEmail](https://github.com/zehm/sendEmail) client in existence, but I would think you’re using the `send-mail-*` options on backup command. Same options work in send-mail command which is a little less noisy if you want to do something like look at the profiling log. I’m not sure it got that far though, as it’s best for showing transcript with a server. You saw what at first glance is a failure to connect, except I can’t reproduce that. What I get from specifying an unreachable host (on local LAN or Internet) is like: ```plaintext 2026-06-04 12:50:14 -04 - [Information-Duplicati.Library.Main.Controller-StartingOperation]: The operation SendMail has started 2026-06-04 12:50:14 -04 - [Profiling-Timer.Begin-Duplicati.Library.Main.Controller-RunSendMail]: Starting - Running SendMail 2026-06-04 12:50:14 -04 - [Profiling-Timer.Finished-Duplicati.Library.Main.Controller-RunSendMail]: Running SendMail took 0:00:00:00.586 2026-06-04 12:50:38 -04 - [Warning-Duplicati.Library.Modules.Builtin.ReportHelper-ReportSubmitError]: Failed to send message: System.Net.Sockets.SocketException: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond. System.Net.Sockets.SocketException (10060): A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond. at Duplicati.Library.Modules.Builtin.SendMail.SendMessage(String subject, String body) at Duplicati.Library.Modules.Builtin.ReportHelper.OnFinish(IBasicResults result, Exception exception) 2026-06-04 12:50:39 -04 - [Information-Duplicati.Library.Main.Controller-CompletedOperation]: The operation SendMail has completed 2026-06-04 12:52:38 -04 - [Information-Duplicati.Library.Main.Controller-StartingOperation]: The operation SendMail has started 2026-06-04 12:52:38 -04 - [Profiling-Timer.Begin-Duplicati.Library.Main.Controller-RunSendMail]: Starting - Running SendMail 2026-06-04 12:52:38 -04 - [Profiling-Timer.Finished-Duplicati.Library.Main.Controller-RunSendMail]: Running SendMail took 0:00:00:00.052 ``` I was hoping for a stack trace showing how it got there. Just end isn’t informative. I also looked in server log at About Duplicati → Logs → Stored. Please check too. What port and encryption plan is Thunderbird using? As an example, here’s mine: ```plaintext Details of selected server: Description: Google Mail Server Name: smtp.gmail.com Port: 465 User Name: me@gmail.com Authentication method: OAuth2 Connection Security: SSL/TLS ``` I have a second Thunderbird “Outgoing server (SMTP)” on port 587 looking like: ```plaintext Authentication method: Normal password Connection Security: STARTTLS ``` Most of that is in the Duplicati `send-mail-url` option. Bubble help is long. CLI: ```plaintext --send-mail-url (String): SMTP Url Use this option to set a URL for the SMTP server, e.g. smtp://example.com:25. Multiple servers can be supplied in a prioritized list, separated with semicolon. If a server fails, the next server in the list is tried, until the message has been sent. If no server is supplied, a DNS lookup is performed to find the first recipient's MX record, and all SMTP servers are tried in their priority order until the message is sent. To enable SMTP over SSL, use the format smtps://example.com. To enable SMTP STARTTLS, use the format smtp://example.com:25/?starttls=when-available or smtp://example.com:25/?starttls=always. If no port is specified, port 25 is used for non-ssl, and 465 for SSL connections. To force not to use STARTTLS use smtp://example.com:25/?starttls=never. ``` [Split Tunnel App Examples](https://helpdesk.privateinternetaccess.com/hc/en-us/articles/46612003321243-Split-Tunnel-App-Examples) shows Thunderbird. Check if you split tunnel yours. Other ways to troubleshoot what might be a network issue (or at least varies) is `netstat -a | grep ` during a `send-mail` command (or timed well if using a `backup` command, but that’s harder). Or create a simple backup. Advanced options can be seen and copied via three dot menu on Options page: ![image](https://forum.duplicati.com/uploads/default/original/2X/2/2877d89d4d97b6bf3c3d3e65fa944840b8a54386.png) If your SMTP server is done by IP (or DNS is slow), use `netstat -an` instead. Either way, is server shown? Non-response will usually show `SYN_SENT` State. ---
**Author:** ![scrognoid](https://forum.duplicati.com/letter_avatar_proxy/v4/letter/s/c4cdca/32.png) [@scrognoid](https://forum.duplicati.com/u/scrognoid)\ **Post date:** [June 6, 2026, 9:38pm UTC](https://forum.duplicati.com/t/sendemail-fail-with-vpn/22445/9 "2026-06-06T21:38:11Z")
I misspoke. sendemail is what LuckyBackup uses. I use duplicati to move those backups to the cloud. Thank you for you detailed reply. But this is not something I need bad enough to try and debug it. I’ll just turn VPN off when I run duplicati.