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    <p>Using Linux or OSx, do what Sorin recommended but use port 465 instead. 25 is the generic SMTP port, but not what GMail uses. Also, I don't believe you want to use -starttls smtp</p> <pre><code>openssl s_client -connect smtp.gmail.com:465 </code></pre> <p>You should get lots of information on the SSL session and the response: </p> <pre><code>220 mx.google.com ... </code></pre> <p>Type in </p> <pre><code>HELO smtp.gmail.com </code></pre> <p>and you'll receive: </p> <pre><code>250 mx.google.com at your service </code></pre> <p>From there it is not quite as straightforward as just sending SMTP messages because Gmail has protections in place to ensure you only send emails appearing to be from accounts that actually belong to you. Instead of typing in "Helo", use "Ehlo". I don't know much about SMTP so I cannot explain the difference, and don't have time to research much. Perhaps someone with more knowledge can explain. </p> <p>Then, type "auth login" and you will receive the following: </p> <pre><code>334 VXNlcm5hbWU6 </code></pre> <p>This is essentially the word "Username" encoded in Base 64. Using a Base 64 encoder such as <a href="http://www.opinionatedgeek.com/dotnet/tools/base64encode/" rel="nofollow noreferrer">this one</a>, encode your user name and enter it. Do the same for your password, which is requested next. You should see: </p> <pre><code>235 2.7.0 Accepted </code></pre> <p>And that's it, you're logged in.</p> <p>There is one more oddity to overcome if you're using OSx or Linux terminals. Just pressing the "ENTER" key does not apparently result in a CRLF which SMTP needs to end a message. You have to use "CTRL+V+ENTER". So, this should look like the following: </p> <pre><code>^M .^M 250 2.0.0 OK </code></pre>
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    1. COFor osx at least, you can add "-crlf" to the initial 'openssl' connection to make it work nicely with RETURNS. e.g. openssl s_client -connect smtp.gmail.com:465 -crlf
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