Azure Virtual Machines
An Azure service that is used to provision Windows and Linux virtual machines.
8,433 questions
please delete this comment. - submitted in error.
A legacy Azure VM previously allowed SMTP with port 2525, but clone of this VM is not allowing traffic on port 2525
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Rob Gunston
1
Reputation point
I was running a legacy VM with Windows 2003 R2 (which cannot be upgraded to a newer OS for reasons). This was functioning fine and able to send SMTP email via Windows IIS Relay and Sendgrid on port 2525 (the older relay cannot handle secure email).
This VM has now been generalized so is no longer running, but I now have cloned the image and have a new iteration of the VM running fine, with the exception of SMTP on port 2525. I cannot see anything that is different in botht he VM and the network/port settings - how do I re-enable port 2525 to send email? Both the old and new VMs are using the same network resource so the settings are identical.
Thanks
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Silvia Wibowo 5,286 Reputation points Microsoft Employee2025-02-26T22:51:52.4166667+00:00 Hi @Rob Gunston , how do you know that port 2525 is not working? What error message did you get? What Windows version are you using on the new VM? What is the output of "netstat -an | findstr 2525" PowerShell command?
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Markapuram Sudheer Reddy 990 Reputation points Microsoft Vendor2025-02-27T16:31:04.9366667+00:00 Hi Rob Gunston,
Thank You for reaching out to Microsoft Q&A forum.
Could you please confirm if you have reviewed the suggestions provided by Silvia Wibowo and please kindly share any outcomes or observations which will help us to investigate further.
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Rob Gunston 1 Reputation point
2025-02-28T00:45:10.91+00:00 Hi, thanks for your reply. The response for "netstat -an | findstr 2525" is:
TCP 0.0.0.0:2525 0.0.0.0:0 LISTENINGWhen I test the connection to sendgrid on port 2525 I get the following:
> telnet smtp.sendgrid.com 2525Connecting To smtp.sendgrid.com...Could not open connection to the host, on port 2525: Connect failedHowever, on my local machine I can connect fine, so it seems to be on the server/Azure side:
Connection to smtp.sendgrid.net port 2525 [tcp/ms-v-worlds] succeeded!It's strange as the connection was fine on the original (now generalized) VM.
Rob
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