authentication failure STARTTLS failed code 220 response: SMTP server ready: Page 2

authentication failure STARTTLS failed code 220 response: SMTP server ready

ntozier

So I've been connecting to o365 with osTicket since 1.10 just fine. I've also used PHP 5.6, 7.0.x, and 7.2.x

Here are the settings I use:

My primary site is currently running 1.14.1 under IIS 8.5 and my PHP version is 7.3.12.

I say this because I'm not sure why you are having an issue with it. Please try matching my settings and see what happens.

emoreno

Thanks for the response!

latest osTicket info from /scp/system.php

Server Information
osTicket Version	v1.12.2 (a5d898b) — v1.12.5 is available
Web Server Software	Microsoft-IIS/10.0
MySQL Version	8.0.17
PHP Version	7.3.7

I don't have [_] Use Separate Authentication. ?

packet dump via WireShark:

packetNumber,time,source,destination,protocol,length,Info
"114","9.996556",osTicketServer,mailServer,"SMTP","70","C: EHLO localhost"
"115","10.025890",mailServer,osTicketServer,"SMTP","165","[TCP Spurious Retransmission] S: 220 SN1PR12CA0109.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 13 Dec 2019 15:16:32 +0000"
"116","10.025935",osTicketServer,mailServer,"TCP","66","[TCP Dup ACK 114#1] 50615 → 587 [ACK] Seq=17 Ack=112 Win=262656 Len=0 SLE=1 SRE=112"
"117","10.026672",mailServer,osTicketServer,"SMTP","258","S: 250-SN1PR12CA0109.outlook.office365.com Hello [XXX.XXX.XXX.XXX] | 250-SIZE 157286400 | 250-PIPELINING | 250-DSN | 250-ENHANCEDSTATUSCODES | 250-STARTTLS | 250-8BITMIME | 250-BINARYMIME | 250-CHUNKING | 250 SMTPUTF8"
"118","10.027100",osTicketServer,mailServer,"SMTP","64","C: STARTTLS"
"119","10.058055",mailServer,osTicketServer,"SMTP","258","[TCP Spurious Retransmission] S: 250-SN1PR12CA0109.outlook.office365.com Hello [XXX.XXX.XXX.XXX] | 250-SIZE 157286400 | 250-PIPELINING | 250-DSN | 250-ENHANCEDSTATUSCODES | 250-STARTTLS | 250-8BITMIME | 250-BINARYMIME | 250-CHUNKING | 250 SMTPUTF8"
"120","10.058084",osTicketServer,mailServer,"TCP","66","[TCP Dup ACK 118#1] 50615 → 587 [ACK] Seq=27 Ack=316 Win=262400 Len=0 SLE=112 SRE=316"
"121","10.058702",mailServer,osTicketServer,"SMTP","83","S: 220 2.0.0 SMTP server ready"
"122","10.059973",osTicketServer,mailServer,"SMTP","571","C: \026\003\001\002\000\001\000\001\374\003\003(H\003b | 9B\274\217\2433\273\002D\305\227\301 \016\274\347\343\260.\241\025a\275\216\265&J\000\000\220\300/\300+\3000\300,\000\236\000\242\000\243\000\237\300'\300#\300\023\300\t\300(\300$\300\024\300 | \000g\0003\000@\000k\0008\0009\000\234\000\235\300\256\300\254\300\242\300\236\0002\300\240\300\234\000<\000/\300\257\300\255\300\243\300\237\000j\300\241\300\235\000=\0005\314\251\314\250\314\252\300]\300a\300W\300S\300\\300`\300V\300R\300s\300w\000\304\000\303\300r\300v\000\276\000\275\000\210\000\207\000E\000D\300Q\300P\000\300\000\272\000\204\000A\000\377\001\000\001C\000\000\000\021\000\017\000\000\f40.97.212.18\000\v\000\004\003\000\001\002\000 | \000\f\000 | \000\035\000\027\000\036\000\031\000\030\000#\000\000\000\026\000\000\000\027\000\000\000 | \0000\000.\004\003\005\003\006\003\b\a\b\b\b\t\b | \b\v\b\004\b\005\b\006\004\001\005\001\006\001\003\003\002\003\003\001\002\001\003\002\002\002\004\002\005\002\006\002\000\025\000\322\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000\000"
"123","10.084661",mailServer,osTicketServer,"SMTP","1514","S:  |  |  |  |  |  | 190123000000Z\027 | 210123120000Z0j1\v0\t\006\003U\004\006\023\002US1\0230\021\006\003U\004\b\023 |  |  |  |  |  |  |  |  |  |  |  | "
"124","10.126130",osTicketServer,mailServer,"TCP","54","50615 → 587 [ACK] Seq=544 Ack=1805 Win=262656 Len=0"
"125","10.131010",mailServer,osTicketServer,"SMTP","1514","[TCP Spurious Retransmission] S:  |  |  |  |  |  | 190123000000Z\027 | 210123120000Z0j1\v0\t\006\003U\004\006\023\002US1\0230\021\006\003U\004\b\023 |  |  |  |  |  |  |  |  |  |  |  | "
"126","10.131072",osTicketServer,mailServer,"TCP","66","[TCP Dup ACK 124#1] 50615 → 587 [ACK] Seq=544 Ack=1805 Win=262656 Len=0 SLE=345 SRE=1805"
"127","10.145610",mailServer,osTicketServer,"SMTP","1514","S:  |  |  |  |  |  |  |  |  |  |  | 150804120000Z\027 | 300804120000Z0K1\v0\t\006\003U\004\006\023\002US1\0250\023\006\003U\004 |  |  |  | "
"128","10.145970",mailServer,osTicketServer,"SMTP","1069","S:  |  |  |  |  |  | "
"129","10.146041",osTicketServer,mailServer,"TCP","54","50615 → 587 [ACK] Seq=544 Ack=4280 Win=262656 Len=0"
"130","10.255198",osTicketServer,mailServer,"TCP","61","50615 → 587 [PSH, ACK] Seq=544 Ack=4280 Win=262656 Len=7 [TCP segment of a reassembled PDU]"
"131","10.285520",mailServer,osTicketServer,"TCP","60","587 → 50615 [FIN, ACK] Seq=4280 Ack=551 Win=1048560 Len=0"
"132","10.285566",osTicketServer,mailServer,"SMTP","60","C: \025\003\003\000\002\002.RSET"
"133","10.315526",mailServer,osTicketServer,"TCP","60","587 → 50615 [RST, ACK] Seq=4281 Ack=557 Win=155216 Len=0"

ntozier

I've asked a dev to take a look at this thread.

emoreno

Thank you. I temporarily tried changing host:port
C:\php\php.ini:1027-1029,
osticket\include\pear\Mail\smtp.php:95-101,
osticket\include\pear\Mail\smtpmx.php:76-85
from localhost:25 to smtp.office.com:587,
I restarted IIS, and I still get EHLO localhost in wireshark when trying to set SMTP settings, so I reverted these latest changes..

ramrajone

emoreno
not sure if this is typo or just missed: from localhost:25 to smtp.office.com:587 should be from localhost:25 to smtp.office365.com:587

KevinTheJedi

@emoreno

I see that you receive the error routines:ssl3_get_record:wrong version number which could be an issue with OpenSSL installed on your server, etc. I'm not too familiar with this error so some googling will give you more information and possibly provide (or point) to a resolution.

Cheers.

harbpaul

Hello, has anyone found a solution to this problem?I can get it to work at all.

Web hosting at Bluehost and using Office365 for emails for many years working without a problem.
Recently I installed osTicket which is amazing (thanks developers), but I can't get it to play nice with Office365. I thought given how popular Office365 is, it would be fairly straightforward. I've searched everywhere with no luck, unless I missed something late one night. I hope someone can help.

Server Information
osTicket Version v1.14.1 (f1e9e88) — Up to date
Web Server Software Apache
MySQL Version 5.6.41
PHP Version 5.6.40

These are the errors I get trying different hostnames that I've found on the forum

smtp.office365.com
authentication failure [SMTP: STARTTLS failed (code: 220, response: TLS go ahead)]

ssl://smtp.office365.com
Failed to connect to ssl://smtp.office365.com:587 [SMTP: Failed to connect socket: fsockopen(): unable to connect to ssl://smtp.office365.com:587 (Unknown error) (code: -1, response: )]

tsl://smtp.office365.com
Failed to connect to tls://smtp.office365.com:587 [SMTP: Failed to connect socket: fsockopen(): unable to connect to tls://smtp.office365.com:587 (Unknown error) (code: -1, response: )]

I tried this patch which actually started sending emails when I disabled SMTP. But they go to junk which isn't very professional and it could possibly stop working at anypoint because it's unsecure.
https://stackoverflow.com/questions/39653578/osticket-and-office365-smtp-authentication-failure/39791653#39791653

emoreno

I used mxtoolbox.com to find the hostname that ends with .mail.protection.outlook.com
Could not get SSL to work, but did get SMTP working without authentication.

harbpaul

@emoreno double check your logs and Default MTA setting. When I disabled authentication, it seemed to accept the settings (even though my server requires authentication), but in fact it was logging and error and defaulting the use PHP mail function. What ended up working for me is the following:

1) Update* osTicket's mail class at /include/pear/Net/SMTP.php changing line 176: $this->socket_options =$socket_options; to $this->socket_options = array('ssl' => array('verify_peer_name' => false));

2) Add the required emails to Cpanel with the same password as in Office365.

3) Use http://www.mail-tester.com/ to test for errors (which led me to fix the following deliverability issues)

      A) Edit the domain SPF record

      B) Add a dmarc TXT record to the domain

Replies by my Agents in the UI go to junk. I'm hoping the SPF record hasn't been updated yet and when it does it will solve the problem.

welltecnologia

harbpaul dont work for me.

I have Microsoft Exchange 2019 in my company....

harbpaul

welltecnologia this worked for my Office365 mail setup. If you host your own exchange servers, you may have other settings that need to be adjusted.

khalidmagdi

welltecnologia any solution you have found?

welltecnologia

harbpaul This problem has been going on for years ...
To this day, they have not found a solution.

Impressive....

I've tried Gmail, nothing works on that ...

I have been struggling with this problem for 3 years ....

welltecnologia

harbpaul GMAIL THIS ERROR, EVER, FOR YEARS.....

authentication failure [SMTP: Invalid response code received from server (code: 535, response: 5.7.8 Username and Password not accepted. Learn more at 5.7.8 https://support.google.com/mail/?p=BadCredentials e16sm10520964qtc.92 - gsmtp)]

harbpaul

@welltecnologia I know gmail can be tricky, it gave me a headache on another system. Since you have been working on this for so long, I'm sure you Enabled Less Secure Apps in your Gmail Settings? Another issue I faced was communication between the Web Host and Office365, they use the same ports and the web host didn't allow SMTP traffic on those ports. That's why I created those emails in my Cpanel to send from the webhost.

anthony1

This patch can solve the issue:

diff -ru osticket.orig/include/pear/Net/SMTP.php osticket.fixed/include/pear/Net/SMTP.php
--- osticket.orig/include/pear/Net/SMTP.php	2020-12-07 19:23:52.000000000 +0100
+++ osticket.fixed/include/pear/Net/SMTP.php	2021-02-13 09:58:08.821455158 +0100
@@ -569,7 +569,7 @@
          * STARTTLS extension, and aren't already connected over a secure
          * (SSL) socket connection. */
         if ($tls && version_compare(PHP_VERSION, '5.1.0', '>=')
-            && extension_loaded('openssl') && isset($this->esmtp['STARTTLS'])
+            && extension_loaded('openssl') && $this->esmtp['STARTTLS']
             && strncasecmp($this->host, 'ssl://', 6) !== 0
         ) {
             /* Start the TLS connection attempt. */

Regards,
Anthony Ananich
https colon slash slash ananich dot pro

gramajola

anthony1 Hi Anthony, i tried to comment line with -- and add other line, bu the problem for me persist. I ve used a PHP 7.4.13 and IIS with Windows Server 2019.
May you help me?

nayeemhassan

/include/pear/Net/SMTP.php

Line 176: Replace $this->socket_options = $socket_options; TO
$this->_socket_options = array('ssl' => array('verify_peer_name' => false));

Line 572: Replace && extension_loaded('openssl') && isset($this->esmtp['STARTTLS']) TO
&& extension_loaded('openssl') && $this->esmtp['STARTTLS']

All problem solved for my case
OSTICKET: 1.15.3.1
PHP: v7.3.25

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