[resolved] Upgraded OS ticket, unable to send via SMTP

PSC-IT

Hi team,
Firstly thank you to the devs for such an amazing product, it has made the ICT Team's job here much easier.
I am having a problem with OFfice365 and sending via SMTP. I have read every post retarding and tried every solution, but I just cant get it working.
Details are :
Windows 2012 R2 server with IIS 6.2
OS ticket (v1.14.1)
PHP 7.3.7
I have set the following in the SMTP settings :

Enable ticked
Hostname
smtp.office365.com

Port Number
587

Authentication Required No

I know that it needs to have Authentication required set to yes, but every time I do i get this error :

authentication failure [SMTP: STARTTLS failed (code: 220, response: 2.0.0 SMTP server ready)]

Please help!

RBGE

PSC-IT Do you have openssl enabled in PHP? If not, you might need to do so. In php.ini, look for the following line:

;extension=php_openssl.dll

and remove the ; from the front. After you restart IIS and enable authentication, see if it makes any difference.

ntozier

Also as a side note, I am pretty sure that smtp.office265.com requires authentication.

PSC-IT

Hi Team,
Thanks for the reply, yes I do have OpenSSL enabled.
Very strange as it was working perfectly before the update :

[PHP_OPENSSL]
extension=php_openssl.dll

ntozier

Your setup is almost identical to mine.

Windows Server 2012 R2, w/ IIS 8
PHP 7.3.12
osTicket 1.14.1
Using with O365.
And it works for me.

Here are my settings.

PSC-IT

Hey Ntozier, thanks for the reply. Agreed it is exactly the same!
Its obviously something I have done during the upgrade.
The error message indicates some kind of OpenSSL error to me.....
IS there anything I need to do with the API keys?
We use smtp on the copiers here and they use port 25 with a SPF record, so no authetication needed.
When I enter these details it doesnt work either.....

Seem to be getting this logged too in the php logfile :
[21-Jan-2020 21:15:42 UTC] PHP Warning: mail(): Failed to connect to mailserver at "localhost" port 25, verify your "SMTP" and "smtp_port" setting in php.ini or use ini_set() in C:\inetpub\osticket\include\pear\Mail\mail.php on line 156

Any suggestions? Thanks in advance!

PSC-IT

Hey guys! Quick update, I have been able to get OS ticket sending via SMTP through the local SMTP server relay here.
When I switch it to smtp.office365.com 587 i still get the StartTLS failed error.
Not as urgent as before, but at least we can notify users when their tickets are logged now.
Thanks in advance for your help!

ntozier

We were using a local smtp relay for a while until we switched to smtp.office.com:587.

Do you use MFA or anything? [If s then the ticket account would have to have it disabled]
Is your we server running a self signed cert or a real cert?
Can you look at the exchange logs to see why STARTTLS is failing?

As a side note have you tried re-entering your username (email) and password in osTicket and see if that helps? (I doubt that it will)

PSC-IT

Hey Ntozier, thanks for the reply
No MFA, and the webserver is not running any SSL certs (when you browse to it it says unsecure)
I will check the exchange logs now.
Thanks for the suggestions!

ramrajone

PSC-IT
What @ntozier has for office365 settings should work, unless you have some kind of local hybrid server doing relay for internal services, then you would have to add your osTickets server to allow to get to office365 service

Energy

This fixed my problem after updating.
Had the same issue :-)

Turn off peer name verification (SMTP)
https://github.com/osTicket/osTicket/commit/4f68aeb3fd746a18c598689b8b428db49faa7613

PSC-IT

Thanks Energy!!!! Looks like thats the same problem I am having!
So do i need to add the code into the smtp.php file at osticket\include\pear\Net ?

PSC-IT

you are a champion Energy!! Thank you sooo much it is now working and we are very happy!
Thanks Ntozier, Ramrajone and Energy for everything, very happy ICT Team here! 😀

Energy

@PSC-IT

You're welcome.

ntozier

So it sounds like you are all set. I'll mar this thread as resolved and close it.
Please feel free to start a new thread if you have another issue or question.