MFA Emails bouncing but test emails and voicemail emails work fine

I’m trying to send the test email for the new MFA module and it’s bouncing. When sending via the debug of the email settings in System Admin, the email is being sent from asterisk@[DOMAIN].com but when it tries to send from the MFA module, it shows as asterisk@[HOST NAME].[DOMAIN].com. and Office 365 rejects that because it’s expecting asterisk@[DOMAIN].com.

PBXact 15.0.37
Current Asterisk Version: 16.30.0

Here is the mail log info:

Apr 13 09:14:29 [HOST NAME] postfix/pickup[5218]: 2C65E8003173: uid=995 from=<asterisk@[HOST NAME]>
Apr 13 09:14:29 [HOST NAME] postfix/cleanup[5082]: 2C65E8003173: message-id=<64382a6516ab3@[HOST NAME]>
Apr 13 09:14:29 [HOST NAME]postfix/qmgr[25354]: 2C65E8003173: from=<asterisk@[HOST NAME].[DOMAIN].com>, size=3726, nrcpt=1 (queue active)
Apr 13 09:14:31 [HOST NAME] postfix/smtp[5089]: warning: smtp.office365.com[52.96.164.242]:587: response longer than 2048: 554 5.2.252 SendAsDenied; aste…
Apr 13 09:14:31 [HOST NAME] postfix/smtp[5089]: 2C65E8003173: to=<todd@[DOMAIN]>, relay=smtp.office365.com[52.96.164.242]:587, delay=2.2, delays=0.06/0.04/1.5/0.63, dsn=5.2.252, status=bounced (host smtp.office365.com[52.96.164.242] said: 554 5.2.252 SendAsDenied; asterisk@[DOMAIN].com not allowed to send as asterisk@[HOST NAME].[DOMAIN].com; STOREDRV.Submission.Exception:SendAsDeniedException.MapiExceptionSendAsDenied; Failed to process message due to a permanent exception with message [BeginDiagnosticData]Cannot submit message. 0.35250:28020000, 1.36674:0A000000, 1.61250:00000000, 1.45378:02000000, 1.44866:4D2C0000, 1.36674:0E000000, 1.61250:00000000, 1.45378:522C0000, 1.44866:E4010000, 16.55847:2B170000, 17.43559:0000000024020000000000000000000000000000, 20.52176:140F9A981E00001050040000, 20.50032:140F9A988E17F01F56000000, 0.53414:55040000, 0.35180:0B004536, 255.23226:0A000000, 255.27962:0A000000, 255.27962:0E000000, 255.31418:1F000130, 0.35250:60040000, 1.36674:0A000000, 1.61250:00000000, 1.45378:02000000, 1.44866:92000000, 1.36674:32000000, 1.61250:00000000, 1.45378:97000000, 1.44866:01000000, 16.55847:0D010000, 17.43559:00000000C8030000000000000000000000000000, 20.52176:140F9A981E0070204800D13D, 20.50032:140F9A988E17101059000000, 0.53414:0A002F3D, 0.35180:83020000, 255.23226:6A000000, 255.27962:0A000000, 255.27962:32000000, 255.17082:DC040000, 0.27745:0A00A880, 4.21921:DC040000, 255.27962:FA000000, 255.1494:03000B67, 0.38698:05000780, 1.41134:46000000, 0.37692:86000000, 0.37948:01000000, 5.33852:00000000534D545000000000, 7.36354:010000000000010986000000, 4.56248:DC040000, 7.40748:010000000000010B86000000, 7.57132:000000000000000000000000, 4.39640:DC040000, 1.63016:32000000, 8.45434:CA24B14656D87448A0F0F61DF09382B2612D3666, 1.46798:04000000, 5.10786:0000000031352E32302E363239382E3033303A445337505231394D42343536383A62363933313165612D366666612D343134312D626535322D3865633065633336396532383A38323135323A2E4E4554204672616D65776F726B20342E382E393033322E30001010A4000000, 7.51330:D342E9293A3CDB0812000000, 0.
Apr 13 09:14:31 [HOST NAME] postfix/cleanup[5082]: 62DA88190F75: message-id=<20230413161431.62DA88190F75@[HOST NAME]>
Apr 13 09:14:31 [HOST NAME] postfix/bounce[5159]: 2C65E8003173: sender non-delivery notification: 62DA88190F75
Apr 13 09:14:31 [HOST NAME] postfix/qmgr[25354]: 62DA88190F75: from=<>, size=9998, nrcpt=1 (queue active)
Apr 13 09:14:31 [HOST NAME] postfix/qmgr[25354]: 2C65E8003173: removed
Apr 13 09:14:31 [HOST NAME] postfix/smtp[5089]: connect to smtp.office365.com[2603:1036:308:283d::2]:587: Network is unreachable
Apr 13 09:14:31 [HOST NAME] postfix/smtp[5089]: connect to smtp.office365.com[2603:1036:308:2825::2]:587: Network is unreachable
Apr 13 09:14:33 [HOST NAME] postfix/smtp[5089]: 62DA88190F75: to=<asterisk@[HOSTNAME].[DOMAIN NAME], relay=smtp.office365.com[52.96.113.178]:587, delay=2.3, delays=0/0/1.8/0.45, dsn=2.0.0, status=sent (250 2.0.0 OK <20230413161431.62DA88190F75@[HOST NAME]> [Hostname=DS7PR19MB4568.namprd19.prod.outlook.com])
Apr 13 09:14:33 PBX-BlackStar postfix/qmgr[25354]: 62DA88190F75: removed

You can possibly bypass messing with getting the correct from email address by setting up a relay connector in your Office 365 tenant (this works well only if you have an external static IP address that your phone system would be coming from).

You want option 3 from this page:

I got this resolved by going to Advanced Settings, User Management Module, Email From Address and entering asterisk@[domain.com] and it worked.

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