following setup: Mail domain cudo.com is running on a mailEnable Windows server.
Now there is an additional Microsoft O365 environment with Exchnage Online and the domain cudo.com is enabled there.
There is a guide from Microsoft that describes which connectors to set up:
I want ALL emails to be sent only through Exchange Online.
The connector "from exchange online to mailEnable" works fine, i.e. when I send an email to a mailEnable mailbox, Exchange Online successfully passes the message to mailEnable.
But what does not work is sending mailEnable via Exchange Online.
I have already tried to change the SMTP settings to enable Smart Host and forward everything to smtp.office365.com.
Unfortunately, I keep getting as response to emails sent:
Reason: 530 5.7.57 Client not authenticated to send mail. [AM6PR05CA0027.eurprd05.prod.outlook.com]
Can anyone help me who has successfully set up this setup before?
Many thanks and best regards
Here are some logs:
Code: Select all
02/25/21 12:47:48 ME-I0018: [B216839EF56D4C088341FE137D8B6BEE.MAI] Outbound message from ([SMTP:J.Doe@cudo.com]) requeued as [B1B0615DC08A47668ABA5C98E77C615F.MAI] to the target domain [yahoo.com] 02/25/21 12:47:48 ME-I0122: [B1B0615DC08A47668ABA5C98E77C615F.MAI] SMTP Server is forwarding all mail (directly) to SMTP Hosts [smtp.office365.com]. 02/25/21 12:47:48 ME-I0026: [B1B0615DC08A47668ABA5C98E77C615F.MAI] Sending message 02/25/21 12:47:48 ME-IXXXX: [B1B0615DC08A47668ABA5C98E77C615F.MAI] DNS resolved to the following record: IP Address=XX.XX.XXX.XX, Family=2, Type=1, Protocol=6 02/25/21 12:47:48 ME-IXXXX: [B1B0615DC08A47668ABA5C98E77C615F.MAI] Failed to set up outbound SSL environment. 02/25/21 12:47:48 ME-I0074:  (Debug) End of conversation 02/25/21 12:47:49 ME-I0074:  (Debug) End of conversation 02/25/21 12:47:53 ME-IXXXX: [B1B0615DC08A47668ABA5C98E77C615F.MAI] Remote server returned a response indicating a permanent error. Server Response: (530 5.7.57 Client not authenticated to send mail. [AM6XXXXXXXXX.eurprd02.prod.outlook.com]**) 02/25/21 12:47:53 ME-E0036: [B1B0615DC08A47668ABA5C98E77C615F.MAI] MAIL FROM command Failed. 02/25/21 12:47:53 SSL recv failed: socket has was closed gracefully by peer before this recv  02/25/21 12:47:53 ME-I0009: [B1B0615DC08A47668ABA5C98E77C615F.MAI] Remote server has closed connection after 0 milliseconds. Server Response: (-) 02/25/21 12:47:53  Send failed (error 10038). Size 6 02/25/21 12:47:53 ME-E0008: [B1B0615DC08A47668ABA5C98E77C615F.MAI] Outbound, could not send the command to the server (error 10038). 02/25/21 12:47:53 ME-E0060: [B1B0615DC08A47668ABA5C98E77C615F.MAI] - Message could not be delivered to target domain (yahoo.com). Message returned to Sender. 02/25/21 12:47:53 ME-I0119: Domain [cudo.com] has used local loopback address [127.0.0.1] because it is hosted locally. 02/25/21 12:47:53 ME-I0026: [B1B0615DC08A47668ABA5C98E77C615F.MAI] Sending message 02/25/21 12:47:53 ME-IXXXX: [B1B0615DC08A47668ABA5C98E77C615F.MAI] DNS resolved to the following record: IP Address=127.0.0.1, Family=2, Type=1, Protocol=0 02/25/21 12:47:53  Successfully started inbound SSL conversation 02/25/21 12:47:53 ME-IXXXX: [B1B0615DC08A47668ABA5C98E77C615F.MAI] Failed to set up outbound SSL environment.