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OfflineI have not really looked into such a matter, because I just assumed they didn't so I can't give you a definite answer but I can say Gmail should not be sending out people's IP addresses everytime they send an email. If they did they would be sued so fast its not even funny.
You are safe to use Gmail. However take note that your First + Last name will be sent with each email. I believe you can turn this off and/or give a fake First + Last name.
OfflineBeware!!! Because of the way email works, the email address of all IPs between (and including) the sender and receiver are logged in whats called the email header. Gmail, Yahoo, and MSN Hotmail(or Live Mail or whatever its called) all include the IP of whoever accessed the webmail client. So basically your IP is on any email you send (and has boon since email was invented.)
The best way to use anonymous email is to setup a email server somewhere where you cant be traced, set up an anonymous domain, and use it. You could also go the webmail route and use Zimbra on said server.
DO NOT USE THE WEB SERVER WITH YOUR PERSONAL WEB SITE UNLESS YOU DONT MIND YOUR EMAIL BEING LINKED TO YOUR WEB SITE. Same with social networking.
OfflineKev93 said:
Beware!!! Because of the way email works, the email address of all IPs between (and including) the sender and receiver are logged in whats called the email header. Gmail, Yahoo, and MSN Hotmail(or Live Mail or whatever its called) all include the IP of whoever accessed the webmail client. So basically your IP is on any email you send (and has boon since email was invented.)
The best way to use anonymous email is to setup a email server somewhere where you cant be traced, set up an anonymous domain, and use it. You could also go the webmail route and use Zimbra on said server.
DO NOT USE THE WEB SERVER WITH YOUR PERSONAL WEB SITE UNLESS YOU DONT MIND YOUR EMAIL BEING LINKED TO YOUR WEB SITE. Same with social networking.
So I am wrong? 


That is what I get for making an uneducated guess.
OfflineTo SKYC, and the rest of us,
I hope I am not too late but here is one way that I know of for you to use 'anonymous email'.
Well, I am sure you guys do know of disposable email address/temporary inboxes. Well, apart from getting less spam, do you know that you can also use these services to spam others (although it is not meant to be done)…Yes, you can spam others using disposable email address/temporary inboxes such as Yopmail.com.
But, you will have to be smart. There is no built-in feature in Yopmail which allows you to send emails to others..What you need to do is to:
1. Using Yopmail, write an email and send it to yourself. For e.g., you are using 123@yopmail.com. From there write an email (blabalabla…) and then, send it to none other than 123@yopmail.com.
2. Check for new email. You should receive the email that you have sent to yourself.
3. Forward you so-called "received" email to your own personal email address (or actually anyone else's email address such as your friends and family).
Theorically, it should work but honestly speaking, I have tried this on my own and it does not work 'YET" . I do not know why but my 'friends' say this worked for them; hence, that's why I am sharing this 'trick' with you guys.
NOTE: With this method, you can "SPAM" others and at the same time be quite "ANONYMOUS". I am not so sure about the IP address issue or anything like that but one thing is for sure, you can hide your information (name, etc.) from people you send emails to.
Enjoy.
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