blocks|key|2877146|text|要通过gmail发送，您需要使用加密连接。仅使用telnet是不可能做到这一点的，但您可以使用openssl等工具|type|unstyled|depth|inlineStyleRanges|entityRanges|offset|length|data|2877147|使用openssl中的starttls选项进行连接，将普通连接转换为加密连接...|2877148|openssl+s_client+-starttls+smtp+-connect+smtp.gmail.com:587+-crlf+-ign_eof|style|BOLD|2877149|或直接连接到ssl套接字...|2877150|openssl+s_client+-connect+smtp.gmail.com:465+-crlf+-ign_eof|2877151|EHLO本地主机|2877152|之后，使用base64编码的用户名/密码向服务器进行身份验证|2877153|普通AG15ZW1haWxAZ21haWwuY29tAG15cGFzc3dvcmQ=+身份验证|2877154|要从命令行中获取以下内容：|2877155|echo+-ne+'\00user@gmail.com\00password'+%7C+base64
AHVzZXJAZ21haWwuY29tAHBhc3N3b3Jk|code-block|syntax|javascript|2877156|然后继续使用"mail+from:“，如示例中所示|2877157|会话示例：|2877158|openssl+s_client+-connect+smtp.gmail.com:465+-crlf+-ign_eof
[...+lots+of+openssl+output+...]
220+mx.google.com+ESMTP+m46sm11546481eeh.9
EHLO+localhost
250-mx.google.com+at+your+service,+[1.2.3.4]
250-SIZE+35882577
250-8BITMIME
250-AUTH+LOGIN+PLAIN+XOAUTH
250+ENHANCEDSTATUSCODES
AUTH+PLAIN+AG5pY2UudHJ5QGdtYWlsLmNvbQBub2l0c25vdG15cGFzc3dvcmQ=
235+2.7.0+Accepted
MAIL+FROM:+<gryphius-demo@gmail.com>
250+2.1.0+OK+m46sm11546481eeh.9
rcpt+to:+<somepoorguy@example.com>
250+2.1.5+OK+m46sm11546481eeh.9
DATA
354++Go+ahead+m46sm11546481eeh.9
Subject:+it+works

yay!
.
250+2.0.0+OK+1339757532+m46sm11546481eeh.9
quit
221+2.0.0+closing+connection+m46sm11546481eeh.9
read:errno=0|2877159|entityMap|0|LINK|mutability|MUTABLE|url|http://slproweb.com/products/Win32OpenSSL.html^0|1B|7|0|0|0|0|22|0|0|0|1N|0|0|8|0|0|17|4|0|0|D|0|0|0|P|0|0|5|0|0^^$0|@$1|2|3|4|5|6|7|1E|8|@]|9|@$A|1F|B|1G|1|1H]]|C|$]]|$1|D|3|E|5|6|7|1I|8|@]|9|@]|C|$]]|$1|F|3|G|5|6|7|1J|8|@$A|1K|B|1L|H|I]]|9|@]|C|$]]|$1|J|3|K|5|6|7|1M|8|@]|9|@]|C|$]]|$1|L|3|M|5|6|7|1N|8|@$A|1O|B|1P|H|I]]|9|@]|C|$]]|$1|N|3|O|5|6|7|1Q|8|@$A|1R|B|1S|H|I]]|9|@]|C|$]]|$1|P|3|Q|5|6|7|1T|8|@]|9|@]|C|$]]|$1|R|3|S|5|6|7|1U|8|@$A|1V|B|1W|H|I]]|9|@]|C|$]]|$1|T|3|U|5|6|7|1X|8|@$A|1Y|B|1Z|H|I]]|9|@]|C|$]]|$1|V|3|W|5|X|7|20|8|@]|9|@]|C|$Y|Z]]|$1|10|3|11|5|6|7|21|8|@$A|22|B|23|H|I]]|9|@]|C|$]]|$1|12|3|13|5|6|7|24|8|@$A|25|B|26|H|I]]|9|@]|C|$]]|$1|14|3|15|5|X|7|27|8|@]|9|@]|C|$Y|Z]]|$1|16|3|-4|5|6|7|28|8|@]|9|@]|C|$]]]|17|$18|$5|19|1A|1B|C|$1C|1D]]]]

to send over gmail, you need to use an encrypted connection. this is not possible with telnet alone, but you can use tools like <a href="http://slproweb.com/products/Win32OpenSSL.html" rel="noreferrer">openssl</a>

either connect using the starttls option in openssl to convert the plain connection to encrypted...

openssl s_client -starttls smtp -connect smtp.gmail.com:587 -crlf -ign_eof

or connect to a ssl sockect directly...

openssl s_client -connect smtp.gmail.com:465 -crlf -ign_eof

EHLO localhost

after that, authenticate to the server using the base64 encoded username/password

AUTH PLAIN AG15ZW1haWxAZ21haWwuY29tAG15cGFzc3dvcmQ=

to get this from the commandline:

<pre><code>echo -ne '\00user@gmail.com\00password' | base64
AHVzZXJAZ21haWwuY29tAHBhc3N3b3Jk
</code></pre>

then continue with "mail from:" like in your example

example session:

<pre><code>openssl s_client -connect smtp.gmail.com:465 -crlf -ign_eof
[... lots of openssl output ...]
220 mx.google.com ESMTP m46sm11546481eeh.9
EHLO localhost
250-mx.google.com at your service, [1.2.3.4]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH
250 ENHANCEDSTATUSCODES
AUTH PLAIN AG5pY2UudHJ5QGdtYWlsLmNvbQBub2l0c25vdG15cGFzc3dvcmQ=
235 2.7.0 Accepted
MAIL FROM: &lt;gryphius-demo@gmail.com&gt;
250 2.1.0 OK m46sm11546481eeh.9
rcpt to: &lt;somepoorguy@example.com&gt;
250 2.1.5 OK m46sm11546481eeh.9
DATA
354 Go ahead m46sm11546481eeh.9
Subject: it works

yay!
.
250 2.0.0 OK 1339757532 m46sm11546481eeh.9
quit
221 2.0.0 closing connection m46sm11546481eeh.9
read:errno=0
</code></pre>

blocks|key|221215|text|不幸的是，当我被迫使用windows服务器时，我无法让openssl以上述答案所建议的方式工作。|type|unstyled|depth|inlineStyleRanges|entityRanges|data|221216|然而，我能够获得一个类似的程序，它的名字叫斯图奈尔(可以从here上下载)。我是从www.tech-and-dev.com得到这个想法的，但我不得不稍微修改一下说明。下面是我所做的：|offset|length|221217|221218|在windows机器上安装telnet客户端。|ordered-list-item|221219|Download+stunnel。(我下载并安装了一个名为stunnel-4.56-installer.exe).|221220|Once的文件，然后您需要找到stunnel.conf配置文件，在我的示例中，它安装到C:\Program+Files+(x86)\stunnel|style|CODE|221221|Then，，您需要在记事本等文本查看器中打开此文件。查找[gmail-smtp]并删除下面客户机行上的分号(在stunnel.conf文件中，以分号开头的每一行都是注释)。你应该会得到类似这样的结果：|221222|221223|gmail-smtp+client+=+yes+accept+=+127.0.0.1:25+connect+=+smtp.gmail.com:465|221224|完成此操作后，请保存stunnel.conf文件并重新加载配置(为此，请使用+GUI程序，然后单击configuration=>Reload).|BOLD|221225|现在你应该已经准备好在windows+telnet客户端中发送电子邮件了！|221226|转到Start=>run=>cmd。|221227|打开cmd后，键入以下内容并按Enter键：|221228|telnet+localhost+25|code-block|syntax|javascript|221229|然后，您应该会看到类似以下内容：|221230|220+mx.google.com+ESMTP+f14sm1400408wbe.2|221231|然后，您需要通过键入以下内容并按enter键进行回复：|221232|helo+google|221233|这将为您提供以下响应：|221234|250+mx.google.com+at+your+service|221235|如果您获得了此信息，则需要键入以下内容并按enter键：|221236|ehlo+google|221237|221238|250-mx.google.com+at+your+service,+[212.28.228.49]
250-SIZE+35651584
250-8BITMIME
250-AUTH+LOGIN+PLAIN+XOAUTH
250+ENHANCEDSTATUSCODES|221239|现在您应该准备好使用您的Gmail详细信息进行身份验证。为此，请键入以下命令并按enter键：|221240|AUTH+LOGIN|221241|221242|334+VXNlcm5hbWU6|221243|这意味着我们已经准备好使用gmail地址和密码进行身份验证。|221244|但是，由于这是一个加密会话，我们将不得不发送以base64编码的电子邮件和密码。要对您的电子邮件和密码进行编码，您可以使用转换程序或在线网站对其进行编码(例如base64或在谷歌上搜索“base64+online+encoding”)。我建议您在完成此操作之前，不要再接触cmd/telnet会话。|221245|例如，test@gmail.com将变为dGVzdEBnbWFpbC5jb20=，而password将变为cGFzc3dvcmQ=|221246|完成此操作后，复制并将转换后的base64用户名粘贴到命令/远程登录会话中，然后按enter键。这将为您提供以下响应：|221247|334+UGFzc3dvcmQ6|221248|现在，将转换后的base64密码复制并粘贴到命令/远程登录会话中，然后按enter键。如果两个登录凭据都正确，则会显示以下响应：|221249|235+2.7.0+Accepted|221250|您现在应按以下格式输入发件人电子邮件(应与用户名相同)，然后按enter键：|221251|MAIL+FROM:<test@gmail.com>|221252|221253|250+2.1.0+OK+x23sm1104292weq.10|221254|现在，您可以按类似格式输入收件人电子邮件地址，然后按enter键：|221255|RCPT+TO:<recipient@gmail.com>|221256|221257|250+2.1.5+OK+x23sm1104292weq.10|221258|现在，您需要键入以下内容并按enter键：|221259|DATA|221260|这应该会给出以下响应：|221261|354++Go+ahead+x23sm1104292weq.10|221262|现在我们可以开始编写消息了！为此，请按以下格式输入您的邮件(提示：在记事本中执行此操作，并将整个邮件复制到命令/远程登录会话中)：|221263|From:+Test+<test@gmail.com>
To:+Me+<recipient@gmail.com>
Subject:+Testing+email+from+telnet
This+is+the+body

Adding+more+lines+to+the+body+message.|221264|完成电子邮件后，请输入一个圆点：|221265|.|221266|221267|250+2.0.0+OK+1288307376+x23sm1104292weq.10|221268|现在，您需要通过键入以下命令并按enter键来结束会话：|221269|QUIT|221270|221271|221+2.0.0+closing+connection+x23sm1104292weq.10
Connection+to+host+lost.|221272|你的电子邮件现在应该在收件人的邮箱里了！|221273|entityMap|0|LINK|mutability|MUTABLE|url|http://www.stunnel.org/downloads.html|1|http://www.tech-and-dev.com/2010/10/sending-email-using-gmail-smtp-server.html|2|http://www5.rptea.com/base64/^0|0|T|4|0|15|K|1|0|0|0|0|F|C|17|U|0|S|C|0|0|0|A|C|12|Y|0|0|11|0|0|I|0|0|M|0|0|0|G|0|0|0|R|0|0|0|B|0|0|0|S|0|0|0|B|0|0|0|1B|0|0|0|B|0|0|0|U|0|0|45|27|6|2|0|0|1T|0|0|1N|0|0|0|1S|0|0|0|12|0|0|0|B|0|0|0|X|0|0|0|B|0|0|0|L|0|0|0|B|0|0|0|1T|0|0|0|G|0|0|0|B|0|0|0|S|0|0|0|B|0|0|0|K|0^^$0|@$1|2|3|4|5|6|7|3U|8|@]|9|@]|A|$]]|$1|B|3|C|5|6|7|3V|8|@]|9|@$D|3W|E|3X|1|3Y]|$D|3Z|E|40|1|41]]|A|$]]|$1|F|3|-4|5|6|7|42|8|@]|9|@]|A|$]]|$1|G|3|H|5|I|7|43|8|@]|9|@]|A|$]]|$1|J|3|K|5|I|7|44|8|@]|9|@]|A|$]]|$1|L|3|M|5|I|7|45|8|@$D|46|E|47|N|O]|$D|48|E|49|N|O]]|9|@]|A|$]]|$1|P|3|Q|5|I|7|4A|8|@$D|4B|E|4C|N|O]]|9|@]|A|$]]|$1|R|3|-4|5|6|7|4D|8|@]|9|@]|A|$]]|$1|S|3|T|5|6|7|4E|8|@]|9|@]|A|$]]|$1|U|3|V|5|6|7|4F|8|@$D|4G|E|4H|N|O]|$D|4I|E|4J|N|W]]|9|@]|A|$]]|$1|X|3|Y|5|6|7|4K|8|@$D|4L|E|4M|N|W]]|9|@]|A|$]]|$1|Z|3|10|5|6|7|4N|8|@$D|4O|E|4P|N|W]]|9|@]|A|$]]|$1|11|3|12|5|6|7|4Q|8|@$D|4R|E|4S|N|W]]|9|@]|A|$]]|$1|13|3|14|5|15|7|4T|8|@]|9|@]|A|$16|17]]|$1|18|3|19|5|6|7|4U|8|@$D|4V|E|4W|N|W]]|9|@]|A|$]]|$1|1A|3|1B|5|15|7|4X|8|@]|9|@]|A|$16|17]]|$1|1C|3|1D|5|6|7|4Y|8|@$D|4Z|E|50|N|W]]|9|@]|A|$]]|$1|1E|3|1F|5|15|7|51|8|@]|9|@]|A|$16|17]]|$1|1G|3|1H|5|6|7|52|8|@$D|53|E|54|N|W]]|9|@]|A|$]]|$1|1I|3|1J|5|15|7|55|8|@]|9|@]|A|$16|17]]|$1|1K|3|1L|5|6|7|56|8|@$D|57|E|58|N|W]]|9|@]|A|$]]|$1|1M|3|1N|5|15|7|59|8|@]|9|@]|A|$16|17]]|$1|1O|3|1H|5|6|7|5A|8|@$D|5B|E|5C|N|W]]|9|@]|A|$]]|$1|1P|3|1Q|5|15|7|5D|8|@]|9|@]|A|$16|17]]|$1|1R|3|1S|5|6|7|5E|8|@$D|5F|E|5G|N|W]]|9|@]|A|$]]|$1|1T|3|1U|5|15|7|5H|8|@]|9|@]|A|$16|17]]|$1|1V|3|1H|5|6|7|5I|8|@$D|5J|E|5K|N|W]]|9|@]|A|$]]|$1|1W|3|1X|5|15|7|5L|8|@]|9|@]|A|$16|17]]|$1|1Y|3|1Z|5|6|7|5M|8|@$D|5N|E|5O|N|W]]|9|@]|A|$]]|$1|20|3|21|5|6|7|5P|8|@$D|5Q|E|5R|N|W]]|9|@$D|5S|E|5T|1|5U]]|A|$]]|$1|22|3|23|5|6|7|5V|8|@$D|5W|E|5X|N|W]]|9|@]|A|$]]|$1|24|3|25|5|6|7|5Y|8|@$D|5Z|E|60|N|W]]|9|@]|A|$]]|$1|26|3|27|5|15|7|61|8|@]|9|@]|A|$16|17]]|$1|28|3|29|5|6|7|62|8|@$D|63|E|64|N|W]]|9|@]|A|$]]|$1|2A|3|2B|5|15|7|65|8|@]|9|@]|A|$16|17]]|$1|2C|3|2D|5|6|7|66|8|@$D|67|E|68|N|W]]|9|@]|A|$]]|$1|2E|3|2F|5|15|7|69|8|@]|9|@]|A|$16|17]]|$1|2G|3|1H|5|6|7|6A|8|@$D|6B|E|6C|N|W]]|9|@]|A|$]]|$1|2H|3|2I|5|15|7|6D|8|@]|9|@]|A|$16|17]]|$1|2J|3|2K|5|6|7|6E|8|@$D|6F|E|6G|N|W]]|9|@]|A|$]]|$1|2L|3|2M|5|15|7|6H|8|@]|9|@]|A|$16|17]]|$1|2N|3|1H|5|6|7|6I|8|@$D|6J|E|6K|N|W]]|9|@]|A|$]]|$1|2O|3|2P|5|15|7|6L|8|@]|9|@]|A|$16|17]]|$1|2Q|3|2R|5|6|7|6M|8|@$D|6N|E|6O|N|W]]|9|@]|A|$]]|$1|2S|3|2T|5|15|7|6P|8|@]|9|@]|A|$16|17]]|$1|2U|3|2V|5|6|7|6Q|8|@$D|6R|E|6S|N|W]]|9|@]|A|$]]|$1|2W|3|2X|5|15|7|6T|8|@]|9|@]|A|$16|17]]|$1|2Y|3|2Z|5|6|7|6U|8|@$D|6V|E|6W|N|W]]|9|@]|A|$]]|$1|30|3|31|5|15|7|6X|8|@]|9|@]|A|$16|17]]|$1|32|3|33|5|6|7|6Y|8|@$D|6Z|E|70|N|W]]|9|@]|A|$]]|$1|34|3|35|5|15|7|71|8|@]|9|@]|A|$16|17]]|$1|36|3|1H|5|6|7|72|8|@$D|73|E|74|N|W]]|9|@]|A|$]]|$1|37|3|38|5|15|7|75|8|@]|9|@]|A|$16|17]]|$1|39|3|3A|5|6|7|76|8|@$D|77|E|78|N|W]]|9|@]|A|$]]|$1|3B|3|3C|5|15|7|79|8|@]|9|@]|A|$16|17]]|$1|3D|3|1H|5|6|7|7A|8|@$D|7B|E|7C|N|W]]|9|@]|A|$]]|$1|3E|3|3F|5|15|7|7D|8|@]|9|@]|A|$16|17]]|$1|3G|3|3H|5|6|7|7E|8|@$D|7F|E|7G|N|W]]|9|@]|A|$]]|$1|3I|3|-4|5|6|7|7H|8|@]|9|@]|A|$]]]|3J|$3K|$5|3L|3M|3N|A|$3O|3P]]|3Q|$5|3L|3M|3N|A|$3O|3R]]|3S|$5|3L|3M|3N|A|$3O|3T]]]]

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. 

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:

<ol>
<li>Install telnet client on the windows box.</li>
<li>Download stunnel. (I downloaded and installed a file called stunnel-4.56-installer.exe).</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>Then, you need to open this file in a text viewer such as notepad. 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:

<pre><code>[gmail-smtp]
client = yes
accept = 127.0.0.1:25
connect = smtp.gmail.com:465
</code></pre>

Once you have done this save the <code>stunnel.conf</code> file and reload the config (to do this use the stunnel GUI program, and click on configuration=>Reload).</li>
</ol>

Now you should be ready to send email in the windows telnet client! 
Go to Start=>run=>cmd.

Once cmd is open type in the following and press Enter: 

<pre><code>telnet localhost 25
</code></pre>

You should then see something similar to the following:

<pre><code>220 mx.google.com ESMTP f14sm1400408wbe.2
</code></pre>

You will then need to reply by typing the following and pressing enter: 

<pre><code>helo google
</code></pre>

This should give you the following response:

<pre><code>250 mx.google.com at your service
</code></pre>

If you get this you then need to type the following and press enter: 

<pre><code>ehlo google
</code></pre>

This should then give you the following response:

<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>

Now you should be ready to authenticate with your Gmail details. To do this type the following and press enter: 

<pre><code>AUTH LOGIN
</code></pre>

This should then give you the following response:

<pre><code>334 VXNlcm5hbWU6
</code></pre>

This means that we are ready to authenticate by using our gmail address and password.

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 ’base64 online encoding’). I reccomend you do not touch the cmd/telnet session again until you have done this. 

For example test@gmail.com would become dGVzdEBnbWFpbC5jb20= and password would become cGFzc3dvcmQ=

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:

<pre><code>334 UGFzc3dvcmQ6
</code></pre>

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:

<pre><code>235 2.7.0 Accepted
</code></pre>

You should now enter the sender email (should be the same as the username) in the following format and press enter: 

<pre><code>MAIL FROM:&lt;test@gmail.com&gt;
</code></pre>

This should give you the following response:

<pre><code>250 2.1.0 OK x23sm1104292weq.10
</code></pre>

You can now enter the recipient email address in a similar format and press enter: 

<pre><code>RCPT TO:&lt;recipient@gmail.com&gt;
</code></pre>

This should give you the following response:

<pre><code>250 2.1.5 OK x23sm1104292weq.10
</code></pre>

Now you will need to type the following and press enter: 

<pre><code>DATA
</code></pre>

Which should give you the following response:

<pre><code>354 Go ahead x23sm1104292weq.10
</code></pre>

Now we can start to compose the message! To do this enter your message in the following format (Tip: do this in notepad and copy the entire message into the cmd/telnet session):

<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>

When you have finished the email enter a dot:

<pre><code>.
</code></pre>

This should give you the following response:

<pre><code>250 2.0.0 OK 1288307376 x23sm1104292weq.10
</code></pre>

And now you need to end your session by typing the following and pressing enter:

<pre><code>QUIT
</code></pre>

This should give you the following response:

<pre><code>221 2.0.0 closing connection x23sm1104292weq.10
Connection to host lost.
</code></pre>

And your email should now be in the recipient’s mailbox!

blocks|key|3091165|text|就像没有人提到的那样--我建议使用一个很棒的工具来实现这个目的--+swaks|type|unstyled|depth|inlineStyleRanges|offset|length|style|BOLD|entityRanges|data|3091166|#+yum+info+swaks
Installed+Packages
Name++++++++:+swaks
Arch++++++++:+noarch
Version+++++:+20130209.0
Release+++++:+3.el6
Size++++++++:+287+k
Repo++++++++:+installed
From+repo+++:+epel
Summary+++++:+Command-line+SMTP+transaction+tester
URL+++++++++:+http://www.jetmore.org/john/code/swaks
License+++++:+GPLv2%2B
Description+:+Swiss+Army+Knife+SMTP:+A+command+line+SMTP+tester.+Swaks+can+test
++++++++++++:+various+aspects+of+your+SMTP+server,+including+TLS+and+AUTH.|code-block|syntax|javascript|3091167|它有很多选择，几乎可以做任何你想做的事情。|3091168|+gmail+:+STARTTLS，SSLv3+(是的，2016年gmail仍然支持sslv3)|3091169|$+echo+"Hello+world"+%7C+swaks+-4+--server+smtp.gmail.com:587+--from+user@gmail.com+--to+user@example.net+-tls+--tls-protocol+sslv3+--auth+PLAIN+--auth-user+user@gmail.com+--auth-password+7654321+--h-Subject+"Test+message"+--body+-
===+Trying+smtp.gmail.com:587...
===+Connected+to+smtp.gmail.com.
<-++220+smtp.gmail.com+ESMTP+h8sm76342lbd.48+-+gsmtp
+->+EHLO+www.example.net
<-++250-smtp.gmail.com+at+your+service,+[193.243.156.26]
<-++250-SIZE+35882577
<-++250-8BITMIME
<-++250-STARTTLS
<-++250-ENHANCEDSTATUSCODES
<-++250-PIPELINING
<-++250-CHUNKING
<-++250+SMTPUTF8
+->+STARTTLS
<-++220+2.0.0+Ready+to+start+TLS
===+TLS+started+with+cipher+SSLv3:RC4-SHA:128
===+TLS+no+local+certificate+set
===+TLS+peer+DN="/C=US/ST=California/L=Mountain+View/O=Google+Inc/CN=smtp.gmail.com"
+~>+EHLO+www.example.net
<~++250-smtp.gmail.com+at+your+service,+[193.243.156.26]
<~++250-SIZE+35882577
<~++250-8BITMIME
<~++250-AUTH+LOGIN+PLAIN+XOAUTH2+PLAIN-CLIENTTOKEN+OAUTHBEARER+XOAUTH
<~++250-ENHANCEDSTATUSCODES
<~++250-PIPELINING
<~++250-CHUNKING
<~++250+SMTPUTF8
+~>+AUTH+PLAIN+AGFhQxsZXguaGhMGdATGV4X2hoYtYWlsLmNvbQBS9TU1MjQ=
<~++235+2.7.0+Accepted
+~>+MAIL+FROM:<user@gmail.com>
<~++250+2.1.0+OK+h8sm76342lbd.48+-+gsmtp
+~>+RCPT+TO:<user@example.net>
<~++250+2.1.5+OK+h8sm76342lbd.48+-+gsmtp
+~>+DATA
<~++354++Go+ahead+h8sm76342lbd.48+-+gsmtp
+~>+Date:+Wed,+17+Feb+2016+09:49:03+%2B0000
+~>+To:+user@example.net
+~>+From:+user@gmail.com
+~>+Subject:+Test+message
+~>+X-Mailer:+swaks+v20130209.0+jetmore.org/john/code/swaks/
+~>
+~>+Hello+world
+~>
+~>
+~>+.
<~++250+2.0.0+OK+1455702544+h8sm76342lbd.48+-+gsmtp
+~>+QUIT
<~++221+2.0.0+closing+connection+h8sm76342lbd.48+-+gsmtp
===+Connection+closed+with+remote+host.|3091170|雅虎:+TLS又名SMTPS，tlsv1.2|3091171|$+echo+"Hello+world"+%7C+swaks+-4+--server+smtp.mail.yahoo.com:465+--from+user@yahoo.com+--to+user@gmail.com+--tlsc+--tls-protocol+tlsv1_2+--auth+PLAIN+--auth-user+user@yahoo.com+--auth-password+7654321+--h-Subject+"Test+message"+--body+-
===+Trying+smtp.mail.yahoo.com:465...
===+Connected+to+smtp.mail.yahoo.com.
===+TLS+started+with+cipher+TLSv1.2:ECDHE-RSA-AES128-GCM-SHA256:128
===+TLS+no+local+certificate+set
===+TLS+peer+DN="/C=US/ST=California/L=Sunnyvale/O=Yahoo+Inc./OU=Information+Technology/CN=smtp.mail.yahoo.com"
<~++220+smtp.mail.yahoo.com+ESMTP+ready
+~>+EHLO+www.example.net
<~++250-smtp.mail.yahoo.com
<~++250-PIPELINING
<~++250-SIZE+41697280
<~++250-8+BITMIME
<~++250+AUTH+PLAIN+LOGIN+XOAUTH2+XYMCOOKIE
+~>+AUTH+PLAIN+AGFhQxsZXguaGhMGdATGV4X2hoYtYWlsLmNvbQBS9TU1MjQ=
<~++235+2.0.0+OK
+~>+MAIL+FROM:<user@yahoo.com>
<~++250+OK+,+completed
+~>+RCPT+TO:<user@gmail.com>
<~++250+OK+,+completed
+~>+DATA
<~++354+Start+Mail.+End+with+CRLF.CRLF
+~>+Date:+Wed,+17+Feb+2016+10:08:28+%2B0000
+~>+To:+user@gmail.com
+~>+From:+user@yahoo.com
+~>+Subject:+Test+message
+~>+X-Mailer:+swaks+v20130209.0+jetmore.org/john/code/swaks/
+~>
+~>+Hello+world
+~>
+~>
+~>+.
<~++250+OK+,+completed
+~>+QUIT
<~++221+Service+Closing+transmission
===+Connection+closed+with+remote+host.|3091172|在过去的5年里，我一直在使用swaks通过gmail从nagios发送电子邮件通知，没有任何问题。|3091173|entityMap^0|Y|5|0|0|0|0|N|0|0|0|M|0|0|0^^$0|@$1|2|3|4|5|6|7|Y|8|@$9|Z|A|10|B|C]]|D|@]|E|$]]|$1|F|3|G|5|H|7|11|8|@]|D|@]|E|$I|J]]|$1|K|3|L|5|6|7|12|8|@]|D|@]|E|$]]|$1|M|3|N|5|6|7|13|8|@$9|14|A|15|B|C]]|D|@]|E|$]]|$1|O|3|P|5|H|7|16|8|@]|D|@]|E|$I|J]]|$1|Q|3|R|5|6|7|17|8|@$9|18|A|19|B|C]]|D|@]|E|$]]|$1|S|3|T|5|H|7|1A|8|@]|D|@]|E|$I|J]]|$1|U|3|V|5|6|7|1B|8|@]|D|@]|E|$]]|$1|W|3|-4|5|6|7|1C|8|@]|D|@]|E|$]]]|X|$]]

As no one has mentioned - I would suggest to use great tool for such purpose - swaks

<pre><code># yum info swaks
Installed Packages
Name : swaks
Arch : noarch
Version : 20130209.0
Release : 3.el6
Size : 287 k
Repo : installed
From repo : epel
Summary : Command-line SMTP transaction tester
URL : http://www.jetmore.org/john/code/swaks
License : GPLv2+
Description : Swiss Army Knife SMTP: A command line SMTP tester. Swaks can test
 : various aspects of your SMTP server, including TLS and AUTH.
</code></pre>

It has a lot of options and can do almost everything you want.

GMAIL: STARTTLS, SSLv3 (and yes, in 2016 gmail still support sslv3)

<pre><code>$ echo "Hello world" | swaks -4 --server smtp.gmail.com:587 --from user@gmail.com --to user@example.net -tls --tls-protocol sslv3 --auth PLAIN --auth-user user@gmail.com --auth-password 7654321 --h-Subject "Test message" --body -
=== Trying smtp.gmail.com:587...
=== Connected to smtp.gmail.com.
&lt;- 220 smtp.gmail.com ESMTP h8sm76342lbd.48 - gsmtp
 -&gt; EHLO www.example.net
&lt;- 250-smtp.gmail.com at your service, [193.243.156.26]
&lt;- 250-SIZE 35882577
&lt;- 250-8BITMIME
&lt;- 250-STARTTLS
&lt;- 250-ENHANCEDSTATUSCODES
&lt;- 250-PIPELINING
&lt;- 250-CHUNKING
&lt;- 250 SMTPUTF8
 -&gt; STARTTLS
&lt;- 220 2.0.0 Ready to start TLS
=== TLS started with cipher SSLv3:RC4-SHA:128
=== TLS no local certificate set
=== TLS peer DN="/C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com"
 ~&gt; EHLO www.example.net
&lt;~ 250-smtp.gmail.com at your service, [193.243.156.26]
&lt;~ 250-SIZE 35882577
&lt;~ 250-8BITMIME
&lt;~ 250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
&lt;~ 250-ENHANCEDSTATUSCODES
&lt;~ 250-PIPELINING
&lt;~ 250-CHUNKING
&lt;~ 250 SMTPUTF8
 ~&gt; AUTH PLAIN AGFhQxsZXguaGhMGdATGV4X2hoYtYWlsLmNvbQBS9TU1MjQ=
&lt;~ 235 2.7.0 Accepted
 ~&gt; MAIL FROM:&lt;user@gmail.com&gt;
&lt;~ 250 2.1.0 OK h8sm76342lbd.48 - gsmtp
 ~&gt; RCPT TO:&lt;user@example.net&gt;
&lt;~ 250 2.1.5 OK h8sm76342lbd.48 - gsmtp
 ~&gt; DATA
&lt;~ 354 Go ahead h8sm76342lbd.48 - gsmtp
 ~&gt; Date: Wed, 17 Feb 2016 09:49:03 +0000
 ~&gt; To: user@example.net
 ~&gt; From: user@gmail.com
 ~&gt; Subject: Test message
 ~&gt; X-Mailer: swaks v20130209.0 jetmore.org/john/code/swaks/
 ~&gt;
 ~&gt; Hello world
 ~&gt;
 ~&gt;
 ~&gt; .
&lt;~ 250 2.0.0 OK 1455702544 h8sm76342lbd.48 - gsmtp
 ~&gt; QUIT
&lt;~ 221 2.0.0 closing connection h8sm76342lbd.48 - gsmtp
=== Connection closed with remote host.
</code></pre>

YAHOO: TLS aka SMTPS, tlsv1.2

<pre><code>$ echo "Hello world" | swaks -4 --server smtp.mail.yahoo.com:465 --from user@yahoo.com --to user@gmail.com --tlsc --tls-protocol tlsv1_2 --auth PLAIN --auth-user user@yahoo.com --auth-password 7654321 --h-Subject "Test message" --body -
=== Trying smtp.mail.yahoo.com:465...
=== Connected to smtp.mail.yahoo.com.
=== TLS started with cipher TLSv1.2:ECDHE-RSA-AES128-GCM-SHA256:128
=== TLS no local certificate set
=== TLS peer DN="/C=US/ST=California/L=Sunnyvale/O=Yahoo Inc./OU=Information Technology/CN=smtp.mail.yahoo.com"
&lt;~ 220 smtp.mail.yahoo.com ESMTP ready
 ~&gt; EHLO www.example.net
&lt;~ 250-smtp.mail.yahoo.com
&lt;~ 250-PIPELINING
&lt;~ 250-SIZE 41697280
&lt;~ 250-8 BITMIME
&lt;~ 250 AUTH PLAIN LOGIN XOAUTH2 XYMCOOKIE
 ~&gt; AUTH PLAIN AGFhQxsZXguaGhMGdATGV4X2hoYtYWlsLmNvbQBS9TU1MjQ=
&lt;~ 235 2.0.0 OK
 ~&gt; MAIL FROM:&lt;user@yahoo.com&gt;
&lt;~ 250 OK , completed
 ~&gt; RCPT TO:&lt;user@gmail.com&gt;
&lt;~ 250 OK , completed
 ~&gt; DATA
&lt;~ 354 Start Mail. End with CRLF.CRLF
 ~&gt; Date: Wed, 17 Feb 2016 10:08:28 +0000
 ~&gt; To: user@gmail.com
 ~&gt; From: user@yahoo.com
 ~&gt; Subject: Test message
 ~&gt; X-Mailer: swaks v20130209.0 jetmore.org/john/code/swaks/
 ~&gt;
 ~&gt; Hello world
 ~&gt;
 ~&gt;
 ~&gt; .
&lt;~ 250 OK , completed
 ~&gt; QUIT
&lt;~ 221 Service Closing transmission
=== Connection closed with remote host.
</code></pre>

I have been using swaks to send email notifications from nagios via gmail for last 5 years without any problem.

blocks|key|226723|text|在现有答案的基础上，本文将逐步介绍如何在命令行中使用GMail帐户通过SMTP发送自动电子邮件，而无需透露密码。|type|unstyled|depth|inlineStyleRanges|entityRanges|data|226724|要求|226725|首先，安装以下软件包：|226726|226727|Expect|unordered-list-item|offset|length|226728|OpenSSL|226729|Core+Utils+(base64)|226730|226731|这些指令假定是Linux操作系统，但应该相当容易移植到Windows+(通过Cygwin或本地等效物)或其他操作系统。|226732|身份验证|226733|将以下shell脚本另存为authentication.sh|style|CODE|226734|#!/bin/bash

#+Asks+for+a+username+and+password,+then+spits+out+the+encoded+value+for
#+use+with+authentication+against+SMTP+servers.

echo+-n+"Email+(shown):+"
read+email
echo+-n+"Password+(hidden):+"
read+-s+password
echo

TEXT="\0$email\0$password"

echo+-ne+$TEXT+%7C+base64|code-block|syntax|javascript|226735|将其设置为可执行文件，并按如下方式运行：|226736|chmod+%2Bx+authentication.sh
./authentication.sh|226737|出现提示时，请提供您的电子邮件地址和密码。这看起来像这样：|226738|Email+(shown):+bob@gmail.com
Password+(hidden):+
AGJvYkBnbWFpbC5jb20AYm9iaXN0aGViZXN0cGVyc29uZXZlcg==|226739|复制最后一行(AGJ...==)，因为它将用于身份验证。|226740|通知|226741|将以下expect脚本另存为notify.sh+(请注意，第一行引用expect程序)：|226742|#!/usr/bin/expect

set+address+"[lindex+$argv+0]"
set+subject+"[lindex+$argv+1]"
set+ts_date+"[lindex+$argv+2]"
set+ts_time+"[lindex+$argv+3]"

set+timeout+10
spawn+openssl+s_client+-connect+smtp.gmail.com:465+-crlf+-ign_eof+

expect+"220"+{
++send+"EHLO+localhost\n"

++expect+"250"+{
++++send+"AUTH+PLAIN+YOUR_AUTHENTICATION_CODE\n"

++++expect+"235"+{
++++++send+"MAIL+FROM:+<YOUR_EMAIL_ADDRESS>\n"

++++++expect+"250"+{
++++++++send+"RCPT+TO:+<$address>\n"

++++++++expect+"250"+{
++++++++++send+"DATA\n"

++++++++++expect+"354"+{
++++++++++++send+"Subject:+$subject\n\n"
++++++++++++send+"Email+sent+on+$ts_date+at+$ts_time.\n"
++++++++++++send+"\n.\n"

++++++++++++expect+"250"+{
++++++++++++++++send+"quit\n"
++++++++++++}
++++++++++}
++++++++}
++++++}
++++}
++}
}|226743|进行以下更改：|226744|226745|使用由authentication+script.|ordered-list-item|226746|Change+YOUR_EMAIL_ADDRESS生成的验证码和用于生成验证码的电子邮件地址粘贴到YOUR_AUTHENTICATION_CODE上。|226747|保存文件。|226748|226749|例如(请注意，电子邮件地址保留尖括号)：|226750|send+"AUTH+PLAIN+AGJvYkBnbWFpbC5jb20AYm9iaXN0aGViZXN0cGVyc29uZXZlcg==\n"
send+"MAIL+FROM:+<bob@gmail.com>\n"|226751|最后，使notify脚本可执行，如下所示：|226752|chmod+%2Bx+notify.sh|226753|发送电子邮件|226754|从命令行发送电子邮件，如下所示：|226755|./notify.sh+recipient@domain.com+"Command+Line"+"March+14"+"15:52"|226756|entityMap|0|LINK|mutability|MUTABLE|url|http://www.nist.gov/el/msid/expect.cfm|1|https://www.openssl.org/source/|2|http://www.gnu.org/software/coreutils/coreutils.html^0|0|0|0|0|0|6|0|0|0|7|1|0|0|A|2|0|0|0|0|D|H|0|0|0|0|0|0|7|8|0|0|E|9|0|0|0|0|0|7|I|1D|O|0|0|0|0|0|0|0|0|0|0^^$0|@$1|2|3|4|5|6|7|2K|8|@]|9|@]|A|$]]|$1|B|3|C|5|6|7|2L|8|@]|9|@]|A|$]]|$1|D|3|E|5|6|7|2M|8|@]|9|@]|A|$]]|$1|F|3|-4|5|6|7|2N|8|@]|9|@]|A|$]]|$1|G|3|H|5|I|7|2O|8|@]|9|@$J|2P|K|2Q|1|2R]]|A|$]]|$1|L|3|M|5|I|7|2S|8|@]|9|@$J|2T|K|2U|1|2V]]|A|$]]|$1|N|3|O|5|I|7|2W|8|@]|9|@$J|2X|K|2Y|1|2Z]]|A|$]]|$1|P|3|-4|5|6|7|30|8|@]|9|@]|A|$]]|$1|Q|3|R|5|6|7|31|8|@]|9|@]|A|$]]|$1|S|3|T|5|6|7|32|8|@]|9|@]|A|$]]|$1|U|3|V|5|6|7|33|8|@$J|34|K|35|W|X]]|9|@]|A|$]]|$1|Y|3|Z|5|10|7|36|8|@]|9|@]|A|$11|12]]|$1|13|3|14|5|6|7|37|8|@]|9|@]|A|$]]|$1|15|3|16|5|10|7|38|8|@]|9|@]|A|$11|12]]|$1|17|3|18|5|6|7|39|8|@]|9|@]|A|$]]|$1|19|3|1A|5|10|7|3A|8|@]|9|@]|A|$11|12]]|$1|1B|3|1C|5|6|7|3B|8|@$J|3C|K|3D|W|X]]|9|@]|A|$]]|$1|1D|3|1E|5|6|7|3E|8|@]|9|@]|A|$]]|$1|1F|3|1G|5|6|7|3F|8|@$J|3G|K|3H|W|X]]|9|@]|A|$]]|$1|1H|3|1I|5|10|7|3I|8|@]|9|@]|A|$11|12]]|$1|1J|3|1K|5|6|7|3J|8|@]|9|@]|A|$]]|$1|1L|3|-4|5|6|7|3K|8|@]|9|@]|A|$]]|$1|1M|3|1N|5|1O|7|3L|8|@]|9|@]|A|$]]|$1|1P|3|1Q|5|1O|7|3M|8|@$J|3N|K|3O|W|X]|$J|3P|K|3Q|W|X]]|9|@]|A|$]]|$1|1R|3|1S|5|1O|7|3R|8|@]|9|@]|A|$]]|$1|1T|3|-4|5|6|7|3S|8|@]|9|@]|A|$]]|$1|1U|3|1V|5|6|7|3T|8|@]|9|@]|A|$]]|$1|1W|3|1X|5|10|7|3U|8|@]|9|@]|A|$11|12]]|$1|1Y|3|1Z|5|6|7|3V|8|@]|9|@]|A|$]]|$1|20|3|21|5|10|7|3W|8|@]|9|@]|A|$11|12]]|$1|22|3|23|5|6|7|3X|8|@]|9|@]|A|$]]|$1|24|3|25|5|6|7|3Y|8|@]|9|@]|A|$]]|$1|26|3|27|5|10|7|3Z|8|@]|9|@]|A|$11|12]]|$1|28|3|-4|5|6|7|40|8|@]|9|@]|A|$]]]|29|$2A|$5|2B|2C|2D|A|$2E|2F]]|2G|$5|2B|2C|2D|A|$2E|2H]]|2I|$5|2B|2C|2D|A|$2E|2J]]]]

Based on the existing answers, here's a step-by-step guide to sending automated e-mails over SMTP, using a GMail account, from the command line, without disclosing the password.

<h1>Requirements</h1>

First, install the following software packages:

<ul>
<li><a href="http://www.nist.gov/el/msid/expect.cfm" rel="nofollow">Expect</a></li>
<li><a href="https://www.openssl.org/source/" rel="nofollow">OpenSSL</a></li>
<li><a href="http://www.gnu.org/software/coreutils/coreutils.html" rel="nofollow">Core Utils</a> (base64)</li>
</ul>

These instructions assume a Linux operating system, but should be reasonably easy to port to Windows (via Cygwin or native equivalents), or other operating system.

<h1>Authentication</h1>

Save the following shell script as <code>authentication.sh</code>:

<pre><code>#!/bin/bash

# Asks for a username and password, then spits out the encoded value for
# use with authentication against SMTP servers.

echo -n "Email (shown): "
read email
echo -n "Password (hidden): "
read -s password
echo

TEXT="\0$email\0$password"

echo -ne $TEXT | base64
</code></pre>

Make it executable and run it as follows:

<pre><code>chmod +x authentication.sh
./authentication.sh
</code></pre>

When prompted, provide your e-mail address and password. This will look something like:

<pre><code>Email (shown): bob@gmail.com
Password (hidden): 
AGJvYkBnbWFpbC5jb20AYm9iaXN0aGViZXN0cGVyc29uZXZlcg==
</code></pre>

Copy the last line (<code>AGJ...==</code>), as this will be used for authentication.

<h1>Notification</h1>

Save the following expect script as <code>notify.sh</code> (note the first line refers to the expect program):

<pre><code>#!/usr/bin/expect

set address "[lindex $argv 0]"
set subject "[lindex $argv 1]"
set ts_date "[lindex $argv 2]"
set ts_time "[lindex $argv 3]"

set timeout 10
spawn openssl s_client -connect smtp.gmail.com:465 -crlf -ign_eof 

expect "220" {
 send "EHLO localhost\n"

 expect "250" {
 send "AUTH PLAIN YOUR_AUTHENTICATION_CODE\n"

 expect "235" {
 send "MAIL FROM: &lt;YOUR_EMAIL_ADDRESS&gt;\n"

 expect "250" {
 send "RCPT TO: &lt;$address&gt;\n"

 expect "250" {
 send "DATA\n"

 expect "354" {
 send "Subject: $subject\n\n"
 send "Email sent on $ts_date at $ts_time.\n"
 send "\n.\n"

 expect "250" {
 send "quit\n"
 }
 }
 }
 }
 }
 }
}
</code></pre>

Make the following changes:

<ol>
<li>Paste over <code>YOUR_AUTHENTICATION_CODE</code> with the authentication code generated by the authentication script.</li>
<li>Change <code>YOUR_EMAIL_ADDRESS</code> with the e-mail address used to generate the authentication code.</li>
<li>Save the file.</li>
</ol>

For example (note the angle brackets are retained for the e-mail address):

<pre><code>send "AUTH PLAIN AGJvYkBnbWFpbC5jb20AYm9iaXN0aGViZXN0cGVyc29uZXZlcg==\n"
send "MAIL FROM: &lt;bob@gmail.com&gt;\n"
</code></pre>

Lastly, make the notify script executable as follows:

<pre><code>chmod +x notify.sh
</code></pre>

<h1>Send E-mail</h1>

Send an e-mail from the command line as follows:

<pre><code>./notify.sh recipient@domain.com "Command Line" "March 14" "15:52"
</code></pre>

For educational purposes, I need to send an email through an SMTP server, using SMTP's fundamental and simple rules. 

I was able to do that using <a href="http://smtp4dev.codeplex.com/">smtp4dev</a>. I <code>telnet localhost 25</code> and and commands are:

<img src="https://i.stack.imgur.com/GkwJ5.png" alt="enter image description here">

I want to do the same thing, using Gmail SMTP server. However, it requires authentication and TLS. I can't figure out how to do that for Gmail. Here's a screenshot of <code>telnet smtp.gmail.com 587</code>:

<img src="https://i.stack.imgur.com/pVLQf.png" alt="enter image description here">

I searched and found many links including <a href="http://en.wikipedia.org/wiki/STARTTLS">Wikipedia's article</a> about <code>STARTTLS</code> command. But I'm not able to use TLS and authenticate to Gmail's SMTP server using command line (or sending commands myself in programming languages). Can anyone help?

How to send email using simple SMTP commands via Gmail?

身份验证

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出于教育目的，我需要使用SMTP的基本和简单规则通过SMTP服务器发送电子邮件。我可以使用做到这一点。I telnet localhost 25和和命令是：​​我想做同样的事情，使用Gmail SMTP服务器。但是，它需要身份验证和TLS。我不知道如何在Gmail上做到这一点。这是telnet smtp.gmail.c...

问如何通过Gmail使用简单的SMTP命令发送电子邮件？
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问如何通过Gmail使用简单的SMTP命令发送电子邮件？
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