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Richard_Steiner
New Member
October 11, 2024
Question

Unable to Establish StartTLS Connection

  • October 11, 2024
  • 1 reply
  • 1049 views

Hello,

 

I have just installed on-premise exchange server and configured hybrid with office365. However, I noticed that I am not able to establish a StartTLS connection with office365 on port 25 and this causes email from on-premise user to a cloud user to fail. I have allowed all services on the firewall policy just to be sure that I am not blocking it but it still fails. I have attached a screenshot of failed connection test form behind fortigate and successful test from outside of Fortigate.

 
No StartTLS.JPGSuccessful StartTLS.JPG
I am a self taught administrator on Fortigate FW and appreciate all the support I can get.
 
Cheers,

~Richard

1 reply

pminarik
Staff
Staff
October 11, 2024

Make sure to run the test through a firewall policy without UTM inspection. To rule out interference from that. Otherwise I'd suggest doing a packet capture of both sides, then check if the replies coming in on WAN differ from what the client sees. It's still plaintext, so it should be easy to read.

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