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When I visited a proxy-check site accessing through a proxy server, I found that my true IP didn’t appear.

But in the header of the mail that I sent—using Thunderbird—accessing through the same proxy server, there appeared my true IP. Why does this phenomenon occur?

In both Firefox and Thunderbird, I check the item “Use this proxy server for all protocols” just below “HTTP Proxy: foorbar”

Here is what the headers look like; my IP would be in the area where there is now [---.---.--.---]:

Received: from [192.168.0.4] (ISP's URL [---.---.--.---])
        by mx.google.com with ESMTPSA id ---------------.0.2015.03.29.--.--.--
        for <[email protected]>

My SMTP server settings on the Thunderbird are:

Port: 465
(Probably I use SMTPS.) and 
Connection Security: SSL/TLS

Also, If the IP of the proxy server is something like 99.99.99.99:8080, then in the SMTP server settings on the Thunderbird, should port number be 8080?

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  • Are you using webmail or an email program? Where in the header is your IP shown?
    – R-D
    Mar 29, 2015 at 16:19
  • Which king of proxy server do you use? [socks/...] Do you use SMTS (port 465) to send emails?
    – AnFi
    Mar 29, 2015 at 16:51

1 Answer 1

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If the kind of proxy you are using is HTTP then you are not able to send emails with that. That is because the mail system uses ports other than 80 but the HTTP proxy can only handle port 80 connections.
Additionally it is good to know that HTTP proxies are not that secure and anonymouse and can be easily tracked down.
Use HTTPS or SOCKS instead.

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