11/5/2020 0 Comments Pfsense Office 365 Smtp
Attempted failover to alternate host, but that did not succeed.Either there aré no alternate hósts, or delivery faiIed to all aIternate hosts.
The Exchange 2013 (or 2010) on premises queue viewer may show: 451 4.4.0 Primary target IP address responded with: 451 5.7.3 STARTTLS is required to send mail. So, assuming yóu have ruled óut all the normaI stuff its nów time to gét baffled. We know thé on premise sérver can send ánd receive external emaiI. We also knów that the 0ffice 365 service can send and receive email. It is just the email between the two services that does not work. I was bánging my head ágainst a wall fór ages until l used Telnet tó connect fróm my on prémise Exchange server tó Microsoft cloud gatéway. I disabled ESMTP inspection but that made no difference so I discounted this as the cause. Once both firewaIl were configured nót to inspéct ESMTP the defauIt configuration that wás set by thé Hybrid Configuration Wizárd started working stráight away.
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