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    <p>Unfortunately as I am forced to use a windows server I have been unable to get openssl working in the way the above answer suggests. </p> <p>However I was able to get a similar program called stunnel (which can be downloaded from <a href="http://www.stunnel.org/downloads.html">here</a>) to work. I got the idea from <a href="http://www.tech-and-dev.com/2010/10/sending-email-using-gmail-smtp-server.html">www.tech-and-dev.com</a> but I had to change the instructions slightly. Here is what I did:</p> <ol> <li>Install telnet client on the windows box.</li> <li>Download stunnel. (I downloaded and installed a file called <em>stunnel-4.56-installer.exe</em>).</li> <li>Once installed you then needed to locate the <code>stunnel.conf</code> config file, which in my case I installed to <code>C:\Program Files (x86)\stunnel</code></li> <li><p>Then, you need to open this file in a text viewer such as <em>notepad</em>. Look for <code>[gmail-smtp]</code> and remove the semicolon on the client line below (in the stunnel.conf file, every line that starts with a semicolon is a comment). You should end up with something like:</p> <pre><code>[gmail-smtp] client = yes accept = 127.0.0.1:25 connect = smtp.gmail.com:465 </code></pre> <p>Once you have done this save the <code>stunnel.conf</code> file and <strong>reload</strong> the config (to do this use the stunnel GUI program, and click on <em>configuration=>Reload</em>).</p></li> </ol> <p>Now you should be ready to send email in the windows telnet client!<br/> Go to <em>Start=>run=>cmd</em>.</p> <p>Once cmd is open type in the following and press Enter: </p> <pre><code>telnet localhost 25 </code></pre> <p>You should then see something similar to the following:</p> <pre><code>220 mx.google.com ESMTP f14sm1400408wbe.2 </code></pre> <p>You will then need to reply by typing the following and pressing enter: </p> <pre><code>helo google </code></pre> <p>This should give you the following response:</p> <pre><code>250 mx.google.com at your service </code></pre> <p>If you get this you then need to type the following and press enter: </p> <pre><code>ehlo google </code></pre> <p>This should then give you the following response:</p> <pre><code>250-mx.google.com at your service, [212.28.228.49] 250-SIZE 35651584 250-8BITMIME 250-AUTH LOGIN PLAIN XOAUTH 250 ENHANCEDSTATUSCODES </code></pre> <p>Now you should be ready to authenticate with your Gmail details. To do this type the following and press enter: </p> <pre><code>AUTH LOGIN </code></pre> <p>This should then give you the following response:</p> <pre><code>334 VXNlcm5hbWU6 </code></pre> <p>This means that we are ready to authenticate by using our gmail address and password.</p> <p>However since this is an encrypted session, we're going to have to send the email and password encoded in base64. To encode your email and password, you can use a converter program or an online website to encode it (for example <a href="http://www5.rptea.com/base64/">base64</a> or search on google for <em>’base64 online encoding’</em>). I reccomend you do not touch the cmd/telnet session again until you have done this. </p> <p>For example <em>test@gmail.com</em> would become <em>dGVzdEBnbWFpbC5jb20=</em> and password would become <em>cGFzc3dvcmQ=</em></p> <p>Once you have done this copy and paste your converted base64 username into the cmd/telnet session and press enter. This should give you following response:</p> <pre><code>334 UGFzc3dvcmQ6 </code></pre> <p>Now copy and paste your converted base64 password into the cmd/telnet session and press enter. This should give you following response if both login credentials are correct:</p> <pre><code>235 2.7.0 Accepted </code></pre> <p>You should now enter the sender email (should be the same as the username) in the following format and press enter: </p> <pre><code>MAIL FROM:&lt;test@gmail.com&gt; </code></pre> <p>This should give you the following response:</p> <pre><code>250 2.1.0 OK x23sm1104292weq.10 </code></pre> <p>You can now enter the recipient email address in a similar format and press enter: </p> <pre><code>RCPT TO:&lt;recipient@gmail.com&gt; </code></pre> <p>This should give you the following response:</p> <pre><code>250 2.1.5 OK x23sm1104292weq.10 </code></pre> <p>Now you will need to type the following and press enter: </p> <pre><code>DATA </code></pre> <p>Which should give you the following response:</p> <pre><code>354 Go ahead x23sm1104292weq.10 </code></pre> <p>Now we can start to compose the message! To do this enter your message in the following format (<strong><em>Tip</em></strong>: do this in notepad and copy the entire message into the cmd/telnet session):</p> <pre><code>From: Test &lt;test@gmail.com&gt; To: Me &lt;recipient@gmail.com&gt; Subject: Testing email from telnet This is the body Adding more lines to the body message. </code></pre> <p>When you have finished the email enter a dot:</p> <pre><code>. </code></pre> <p>This should give you the following response:</p> <pre><code>250 2.0.0 OK 1288307376 x23sm1104292weq.10 </code></pre> <p>And now you need to end your session by typing the following and pressing enter:</p> <pre><code>QUIT </code></pre> <p>This should give you the following response:</p> <pre><code>221 2.0.0 closing connection x23sm1104292weq.10 Connection to host lost. </code></pre> <p>And your email should now be in the recipient’s mailbox!</p>
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