The StartTLS replacement for the old telnet to SMTP server on port 25

When you need to troubleshoot SMTP issues, it is a known fact that a simple telnet to port 25 of the SMTP server in question would get you far. It will get you to see the problems.

When connecting to Office365 ( to relay mail, and you want to check how things work, you can use openssl to wrap in StartTLS your old telnet connection by running this:

openssl s_client -starttls smtp -crlf -connect

From there, you can run your plain old “ehlo user” and all these commands like you are used to.

Just a small note about authentication: if you are facing SMTP which requires authentication, there are few methods you can use. Let’s assume your user is ‘[email protected]’ and your password is ‘password’.

If you are allowed to use the PLAIN method, you need to generate the login/password string into base64, like this:

perl -MMIME::Base64 -e ‘print encode_base64(“\000user\\000password”)’

You could use shell with base64 command to perform the convertion:

echo -ne ‘\[email protected]\0password’ | base64

The result would be a string similar in shape to this: AHVzZXJAZG9tYWluLmNvbQBwYXNzd29yZA==

Then enter the SMTP server at the right prompt:


If you are allowed to use the LOGIN method, you need to generate base64 string for your user and your password separately, like this:

perl -MMIME::Base64 -e ‘print encode_base64(“user\”)’


echo -ne ‘[email protected]’ | base64

The result is dXNlckBkb21haW4uY29t

Same goes for the password field. Choose which of the next two lines you wish to use:

perl -MMIME::Base64 -e ‘print encode_base64(“password”)’

echo -ne ‘password’ | base64

The result is cGFzc3dvcmQ=

Now, for the prompt, we will run:


We’ll get the base64 query for username, so we just type/paste the user base64, and press on Enter. Then we’ll get the base64 prompt for password, so we will type/paste the password base64, and press Enter.

That’s all.

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