[resolved] Authentication Error - Second Email Account

pstarnes

osTicket Versionv1.10.1 (9ae093d) — Up to dateWeb Server SoftwareApache/2.4.18 (Ubuntu)MySQL Version5.7.21PHP Version5.6.34-1+ubuntu16.04.1+deb.sury.org+1I'm running Ubuntu 16.04.4 with Apache/MySql/PHP as shown above. I am also using the LDAP plugin (not sure where to find version number for it, but it is the most current release available on the download link now.)I have one email account configured and working with no problems under Staff/Emails (http://helpdesk/scp/emails.php)Tickets are created in the correct department and I get no errors. Everything works great. This is an Office365 hosted domain.The problem is that when I try to add a second email account by clicking on Add New Email and entering the exact same settings I used on the first account (changing only the username and password) I get the following error:Sending Email via SMTP authentication failure [SMTP: Invalid response code received from server (code: 535, response: 5.7.3 Authentication unsuccessful The settings I'm using:IMAPhostname: outlook.office365.comport: 993protocol: IMAP+SSLSMTPhostname: smtp.office365.comport: 587 (also tested 465)Auth Required: YesI have also tested adding a GMail account with the same results. It seems odd that the first account works just fine but I can't add a second account. I have verified that the server is allowed to communicate with the mail server and that the account credentials are correct.I also set Sending Email via SMTP to disabled and was able to add the account, it's only an issue with SMTP.There is nothing in the System LogsAny suggestions to point me in the right direction?Thanks!Pete

ntozier

is IMAP or POP enabled for the user account?

pstarnes

The account has IMAP and POP enabled in the app settings on the Office365 admin portal.IMAP does work when I enable only Fetching I can add the account. It's only when I try to enable SMTP that I receive the error:Failed to connect to smtp.office365.com This first account I was able to add uses the exact same settings and is hosted on the same Office365 account/domain. I will be doing some more troubleshooting today. Any suggestions are greatly appreciated.Pete

pstarnes

Sorry, it won't let me edit the comment above to change the error message. The actual error message I'm getting is:authentication failure [SMTP: Invalid response code received from server (code: 535, response: 5.7.3 Authentication unsuccessful The error I posted above in the previous comment is what I receive when change to port 465.Sorry for the confusion.

ntozier

The image that you attached is so small I can't read it.It looks like "SN4PR0201CA0031.namprd02.prod.outlook.com" rejected the username and password.I recall something about microsoft saying that they will require tls/ssl for sending mail through o365. Try adding the tls:// or ssl:// prefix?We use the SMTP service on a local server to relay our mail to o365 Exchange so we dont have to fight with o365.

pstarnes

The attachment just showed that IMAP and POP were both enabled for the account on Office365. That wouldn't really explain why one email account works and I only have problems adding another email account on the same server/domain with same settings though.Thanks for the suggestions though. I feel I must be missing something obvious since so many seem to be running this configuration without issue.I tried both the ssl:// and tls:// prefix and get the following errors:( ! ) Warning: stream_socket_client(): SSL operation failed with code 1. OpenSSL Error messages: error routines version number in /var/www/html/include/pear/Net/Socket.php on line 166Warning: stream_socket_client(): Failed to enable crypto in /var/www/html/include/pear/Net/Socket.php on line 166Warning: stream_socket_client(): unable to connect to ssl://smtp.office365.com (Unknown error) in /var/www/html/include/pear/Net/Socket.php on line 166Warning: Cannot modify header information - headers already sent by (output started at /var/www/html/include/pear/Net/Socket.php) in /var/www/html/include/staff/header.inc.php on line 2

ntozier

"That wouldn't really explain why one email account works and I only have problems adding another email account on the same server/domain with same settings though."You are correct, it does not. But then it also doesn't explain why I have six emails on the same server/domain configured in my production site with out the problem that you are reporting."I tried both the ssl:// and tls:// prefix and get the following errors:"Okay I didn't think that would help honestly, but wanted to see ifit resulted in a different error altogether. Take a look at these:try to disable the peer verification: https://github.com/osTicket/osTicket/issues/2628#issuecomment-152526405 or update the pear package components: https://github.com/osTicket/osTicket/issues/3726#issuecomment-344398410

pstarnes

Problem is resolved. I have no idea what resolved it though. After adding the tls and sls prefixes, I removed those and tried again. It worked. Perhaps I had a space or some unseen ascii character in front of smtp.office365.com?! But that doesn't add up because I was getting a reject back from the mail server. In any case you can close this and thanks for troulbeshooting with me on a problem that I know you knew didn't exist! :) Pete

ntozier

Very welcome. :) I'll mark this as closed and resolved. Please feel free to start a new thread if you have another question, etc .