Setting up Microsoft 365 email - Not working OAuth2

Bweleeno

Hello,

I am running osTicket 1.18 and i cannot get my email to work. I was able to follow the guides online for OAuth2 and got the authentication configured. for the remote mailbox tab section, i was able to use IMAP on outlook.office365.com port 993. However, when i test it out, it is not fetching emails.

also, for SMTP, no matter what i try, i always get the same error:
cannot connect to host; error = stream_socket_client(): Unable to connect to tcp://smtp-mail.outlook.com:587 (Connection timed out) (errno = 0 )

i have tried port 25, port 465, & port 587. all results in the same error.

Just to note, i am hosting the website on godaddy & the email is an office exchange email through godaddy & SMTP has been enabled + the OAuth2 requirements.

i have looked online to see what could cause the issue, and they are saying it is due to godaddy hosting. however, i am not sure how can i check if the ports are open on godaddy or not.

any help is appreciated

KevinTheJedi

Bweleeno

You enabled fetching at the mailbox level but did you enable it globally (Admin Panel > Emails > Settings > Email Fetching)? Also, did you create a cron job like the documentation states? In order for mail to fetch you must have fetching enabled globally, you must have a proper IMAP/POP3 setup, you must have fetching enabled at the mailbox level, and must have a cron job setup to continuously poll the mailbox.

Since you are running this on GoDaddy servers you'd simply reach out to their support and ask them if External SMTP is enabled and allowed for your server and if so if port 587 is open.

Cheers.

Bweleeno

KevinTheJedi thanks for the quick response. I did not create a cron job. so i need to do that. but i will leave it for later as godaddy is hell to work with but we are stuck with it.

I looked into the godaddy ports. and i was able to create a small test php to check if it is open. it is not, neither are the rest. Godaddy states it is to prevent scams, and i cannot open it since this is a shared hosting. so i am out of luck in that regard.

however, i looked at options like resend.com which will work since it is routed through HTTPs. do you know how i can modify the code to get to work. i am mainly looking for the send function to modify it with the resend api parameters.

KevinTheJedi

Bweleeno

You will definitely need to modify the code to get this to work. When modifying the codebase you are always on your own as you are deviating from core. The code is open source and publicly available on Github. Github has a great search tool and even a code tree/glossary that aids in navigating the code. You will proceed at your own risk. Just search for "n send(" and go from there. I will say that it's a part of the core class; not any dependencies.

Cheers.

KevinTheJedi

Bweleeno

Actually, try to use GoDaddy's relay server first before you go that route. I think it's included with every plan but you'll need to check and see:

https://www.godaddy.com/help/send-form-mail-using-an-smtp-relay-server-953

Click the Managed Hosting for WordPress / Windows Hosting (Plesk) section in the above link to see the host information. For the SMTP information in osTicket the Status should be set to Enable, Hostname should be relay-hosting.secureserver.net, Port Number should be 25, and Authentication should be set to None - No Authentication Required.

Cheers.

Bweleeno

KevinTheJedi thanks for the help. i tried it but i still get the same issue. However, i did notice that i can send emails in my current setup to an external gmail account (Admin panel -> Emails -> Diagnostic -> Test Outgoing Email) but not to my company emails (godaddy office 365). could there be another reason for this on the email side that i can create an exception for osticket in?

KevinTheJedi

Bweleeno

Well if you don’t have smtp configured and enabled then the web server is sending mail on your behalf via something like send mail or postfix. That’s likely not configured properly so your mail will be seen as spam. Gmail is more lenient on things than Microsoft. So I would check the mail headers to see if it’s passing spf/dkim and if not that’s why.

Cheers.

Bweleeno

KevinTheJedi below is the original mail header

Since gmail is more lenient, could i add an exception on microsoft for the ip address to allow it to pass or is this not possible?

KevinTheJedi

Bweleeno

Wait, so you do have SMTP setup?

Cheers.

Bweleeno

KevinTheJedi nope this is what is weird. when i go to set it up, it shows the connection time out error. but as soon i did have OAuth2 - Microsoft and logged in successfully. below is a snippet from the emails settings for SMTP.

Bweleeno

KevinTheJedi I was able to get SMTP working. i had to use the below settings as provided by Godaddy support. However, i still can't receive emails on my office 365 emails. only on my personal gmail. Any ideas?

Bweleeno

Bweleeno Even i am checking the message traces and i cannot find any mention of quarantined emails from the system email or failed emails. there is zero mention. so i am not sure why they are not showing

KevinTheJedi

Bweleeno

That would likely be an issue on the Microsoft end. Likely a spam trap or something. Cont act your mail admin for further assistance. If you are the admin then do a message trace or look at your quarantine.

Cheers.

Bweleeno

KevinTheJedi thank you so much for the help. i am an admin for office 365. i already did a message trace and looked at the quarantine. no mention of the emails coming from the system email. i am checking the filters now. but it is now clear to me that the issue is from O365's side.

i will see what i can do to allow the emails to pass through. once i find it i will update this thread so that others are aware.

Bweleeno

KevinTheJedi Hello, just so that anybody facing issues with godaddy email sending to internal emails (email1@company.com to email2@company.com) below are the steps needed to rectify it.

Firsty, if you are using a shared hosting, only port 25 will be open and you need to use localhost with no authentication. as per the below photo for SMTP

you have to then use OAuth2 for authentication the remote mailbox for fetching tickets (it connects, but i did not implement it as we decided that we will not need it as this is an internal ticketing system for company requests)

Then you should send a test email. if the test email fails, Ensure that email routing is configured properly
I am using cpanel, so you have to open cpanel -> Emails -> Email Routing & you need to select Remote Mail Exchanger This is especially important if you had webmail before migrating to O365 with godaddy as godaddy will try to route all incoming emails to @company.com to its internal servers first before remote servers. enabling this option will allow you to skip the internal webmail servers first.

Note: this was the main reason i was not getting any message traces for the sent emails, as they were being redirected to godaddy's server & sent to the webmail which is no longer active.

Note: you may need to adjust your DNS settings as well to add office365 to your domain. i did that but it didn't solve the problem. then i did the remail routing which finally resolved the issue.