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<p>GMail does not allow you to use AUTH LOGIN as the authentication
method with your actual GMail password. Thunderbird gets around it
by setting up an OAUTH2 token the first time you connect and using
that instead (which is GMail's preferred authentication method for
third party clients).</p>
<p>In order to use GMail for SMTP, you need to do the following:</p>
<ol>
<li>Make sure your Google account has a second factor
authentication configured</li>
<li>Set up an Application Password for Bugzilla to use.</li>
</ol>
<p>Then you give that application password (which is different from
your normal GMail password) to Bugzilla as the SMTP password.</p>
<p>See <a class="moz-txt-link-freetext" href="https://support.google.com/accounts/answer/185833?hl=en">https://support.google.com/accounts/answer/185833?hl=en</a><br>
</p>
<p><br>
</p>
<div class="moz-cite-prefix">On 2/24/23 7:24 PM, Mike Ambrose wrote:<br>
</div>
<blockquote type="cite"
cite="mid:SJ0PR08MB79300C6174B39F95E9F6829F87A99@SJ0PR08MB7930.namprd08.prod.outlook.com">
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<p class="MsoNormal">Hi,<o:p></o:p></p>
<p class="MsoNormal">I followed the instructions for installing
Bugzilla 5.0.6 on Ubuntu 22.0.4. There was a little tweaking
required for Apache but Bugzilla is now being served by an
Ubuntu server. The big problem is enabling email. I wanted
to use gmail as much easier than setting up our own SMTP
server but it fails to authenticate. Ufw is disabled.
<o:p></o:p></p>
<ul type="disc">
<li class="MsoNormal"
style="mso-margin-top-alt:auto;mso-margin-bottom-alt:auto;mso-list:l0 level1 lfo1">
mail_delivery_method: SMTP<o:p></o:p></li>
<li class="MsoNormal"
style="mso-margin-top-alt:auto;mso-margin-bottom-alt:auto;mso-list:l0 level1 lfo1">
mailfrom: <a href="mailto:new_gmail_address@gmail.com"
moz-do-not-send="true" class="moz-txt-link-freetext">new_gmail_address@gmail.com</a><o:p></o:p></li>
<li class="MsoNormal"
style="mso-margin-top-alt:auto;mso-margin-bottom-alt:auto;mso-list:l0 level1 lfo1">
smtpserver: smtp.gmail.com:465 (I also tried port 587)<o:p></o:p></li>
<li class="MsoNormal"
style="mso-margin-top-alt:auto;mso-margin-bottom-alt:auto;mso-list:l0 level1 lfo1">
smtp_username: <a href="mailto:new_gmail_address@gmail.com"
moz-do-not-send="true" class="moz-txt-link-freetext">new_gmail_address@gmail.com</a><o:p></o:p></li>
<li class="MsoNormal"
style="mso-margin-top-alt:auto;mso-margin-bottom-alt:auto;mso-list:l0 level1 lfo1">
smtp_password: new_gmail_password<o:p></o:p></li>
<li class="MsoNormal"
style="mso-margin-top-alt:auto;mso-margin-bottom-alt:auto;mso-list:l0 level1 lfo1">
smtp_ssl: On<o:p></o:p></li>
</ul>
<p class="MsoNormal">I tested these settings using Thunderbird
on the same server and it works. I also tried some things I
found on the internet including changing the username spec to
user, all to know avail. The following is what Apache
reports:<o:p></o:p></p>
<p class="MsoNormal"><o:p> </o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)<<<
220 smtp.gmail.com ESMTP
m2-20020a056870030200b0016dbf59175bsm95354oaf.47 - gsmtp<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)>>>
EHLO bugzilla-sw<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)<<<
250-smtp.gmail.com at your service, [12.35.227.202]<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)<<<
250-SIZE 35882577<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)<<<
250-8BITMIME<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)<<<
250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER
XOAUTH<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)<<<
250-ENHANCEDSTATUSCODES<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)<<<
250-PIPELINING<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)<<<
250-CHUNKING<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)<<<
250 SMTPUTF8<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)>>>
AUTH LOGIN<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)<<<
334 VXNlcm5hbWU6<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)<<<
(decoded) Username:<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)>>>
(decoded) <a href="mailto:my_gmail@gmail.com"
moz-do-not-send="true" class="moz-txt-link-freetext">
my_gmail@gmail.com</a><o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)>>>
dHB6YnVnc0BnbWFpbC5jb20=<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)<<<
334 UGFzc3dvcmQ6<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)<<<
(decoded) Password:<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)>>>
(decoded) my_password<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)>>>
WXVtIEJ1Z3Mh<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)<<<
535-5.7.8 Username and Password not accepted. Learn more at<o:p></o:p></p>
<p class="MsoNormal">Net::SMTP::_SSL=GLOB(0x562c48a326a0)<<<
535 5.7.8 <a
href="https://support.google.com/mail/?p=BadCredentials"
moz-do-not-send="true" class="moz-txt-link-freetext">
https://support.google.com/mail/?p=BadCredentials</a>
m2-20020a056870030200b0016dbf59175bsm95354oaf.47 – gsmtp<o:p></o:p></p>
<p class="MsoNormal"><o:p> </o:p></p>
<p class="MsoNormal">Does anyone have an idea what is happening
here?<o:p></o:p></p>
<p class="MsoNormal"><o:p> </o:p></p>
<p class="MsoNormal">Thanks,<o:p></o:p></p>
<p class="MsoNormal"><o:p> </o:p></p>
<p class="MsoNormal">Mike Ambrose<o:p></o:p></p>
<p class="MsoNormal">Topaz Systems, Inc<o:p></o:p></p>
<p class="MsoNormal"><o:p> </o:p></p>
</div>
<br>
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