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Brett53559 avatar Server

Why won't exchange authenticate user in admin role?

jp flag
Brett53559

I have a java spring boot application that I authenticate through our exchange servers. The from address included in the email is the same address associated with the authenticated user.

When I point the connection URL directly at one of the exchange servers it will authenticate and send email successfully. However when I point it at the (I think it's called a relay) [URL that points at either server] and then it starts giving me this error (Authentication failed; nested exception is javax.mail.AuthenticationFailedException: 535 5.7.3 Authentication unsuccessful)

At this point the user account is not included within any admin roles. HOWEVER, when I add the account to the "Organization Management" Admin Role which has the following assigned roles (below) it will authenticate and send emails. The final kicker is when I create a copy of that role and add the account as a member, it fails to authenticate. I all these things mentioned above were done while being logged into the domain administrator account with full access. I don't know where else to look or what else to try. Please help.

  • Active Directory Permissions
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  • Cmdlet Extension Agents
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  • Data Loss Prevention
  • Database Availability Groups
  • Database Copies
  • Databases
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  • Exchange Connectors
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  • Org Custom Apps
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  • Organization Client Access
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  • POP3 And IMAP4 Protocols
  • Public Folder Replication
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  • Recipient Policies
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  • Retention Management
  • Role Management
  • Security Admin
  • Security Group Creation and Membership
  • Security Reader
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  • UM Mailboxes
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  • WorkloadManagement
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cn flag
Linuxx
I'm not really sure I fully understand the question. I assume your application wants to send email through the Exchange server. If that's the case, than you can create a connector that specifies your sending application IP that will allow anonymous relay from your application (technically from that server). Assuming you are attempting to relay through an edge gateway, this should do the trick. Here is how to do that on Exchange 2016 https://practical365.com/exchange-2016-smtp-relay-connector/
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