# TLS/SSL SMTP fail regardless of port/tls/ssl

**URL:** <https://forum.pritunl.com/t/tls-ssl-smtp-fail-regardless-of-port-tls-ssl/3761>\
**Category:** Pritunl\
**Created:** [March 26, 2026, 10:23pm UTC](https://forum.pritunl.com/t/tls-ssl-smtp-fail-regardless-of-port-tls-ssl/3761 "2026-03-26T22:23:00Z")\
**Posts on this page:** 2\
**Page:** 1

<div class="post-metadata">

**Author:** ![Wob](https://forum.pritunl.com/user_avatar/forum.pritunl.com/wob/32/1480_2.png) [@Wob](https://forum.pritunl.com/u/Wob)\
**Post date:** [March 26, 2026, 10:23pm UTC](https://forum.pritunl.com/t/tls-ssl-smtp-fail-regardless-of-port-tls-ssl/3761/1 "2026-03-26T22:23:00Z")

</div>

Attempting to set up smtp, unable to get any combination of settings to work.

Using SMTP2GO, have tried all ports (:25, 2525, 587, 465, 443) - all attempts fail and appear to indicate that the python version used by Pritunl is outdated, though the server’s python version is updated (3.12).

Tested via a 365-connector / port25 and was able to get this to connect, but unable to get anything beyond this error when using smtp2go.

File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/pritunl/handlers/user.py”, line 724, in user\_put  
user.send\_key\_email(utils.get\_url\_root())  
File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/pritunl/user/user.py”, line 1667, in send\_key\_email  
utils.send\_email(  
File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/pritunl/utils/mail.py”, line 40, in send\_email  
smtp\_conn.starttls(context=context)  
File “/usr/lib/pritunl/usr/lib/python3.9/smtplib.py”, line 790, in starttls  
self.sock = context.wrap\_socket(self.sock,  
File “/usr/lib/pritunl/usr/lib/python3.9/ssl.py”, line 501, in wrap\_socket  
return self.sslsocket\_class.\_create(  
File “/usr/lib/pritunl/usr/lib/python3.9/ssl.py”, line 1076, in \_create  
self.do\_handshake()  
File “/usr/lib/pritunl/usr/lib/python3.9/ssl.py”, line 1345, in do\_handshake  
self.\_sslobj.do\_handshake()  
ssl.SSLError: [SSL: SSLV3\_ALERT\_ILLEGAL\_PARAMETER] sslv3 alert illegal parameter (\_ssl.c:1147)

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<div class="post-metadata">

**Author:** ![zach](https://forum.pritunl.com/user_avatar/forum.pritunl.com/zach/32/1105_2.png) [@zach](https://forum.pritunl.com/u/zach)\
**Post date:** [March 28, 2026, 8:43pm UTC](https://forum.pritunl.com/t/tls-ssl-smtp-fail-regardless-of-port-tls-ssl/3761/2 "2026-03-28T20:43:17Z")

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This has been fixed in [**pritunl/pritunl@963f850**](https://github.com/pritunl/pritunl/commit/963f8502e794b4dcffe3786a6ccaa0d42e4a8ac2) and will be included in the next release. The file can be manually patched by editing `/usr/lib/pritunl/usr/lib/python3.9/site-packages/pritunl/utils/mail.py` then running `sudo systemctl restart`.