How To Send Mail As Hotmail (smtp.live.com) in Gmail

Gmail has added support for send mail through custom domain SMTP servers feature, which allows Gmail to send mail using custom “From:” of another email address as sender instead of default Gmail e-mail address (which include in Sender field and may be displayed as delivery on behalf of actual email address) that been used to send the message. With Send Mail As custom “From:” sender feature, recipients will not notice that the mail is sent from Gmail, but will be actual true identity of the external email address.

When configuring Gmail to send mail through Windows Live Hotmail outbound SMTP server using the recommended Hotmail SMTP settings as listed below, the settings doesn’t work and cannot pass Gmail verification.

SMTP server: smtp.live.com
Port: 25
Username: [username]@hotmail.com
Password: [password]
Always use a secure connection (SSL) when sending mail: Yes (Check)

After adding above SMTP configuration settings for Hotmail in Gmail, the following error message is returned by Gmail:

Couldn’t reach server. Please double-check the server and port number.

Change the SMTP port to 587 also yields the same error result. When connecting at port 465, Gmail hangs a while when checking credentials, and then return the following error:

Your other email provider is responding too slowly. Please try again later, or contact the administrator of your other domain for further information.

It seems that there is problem or issue with Gmail, which cannot access and connect to smtp.live.com using SSL. Thus, in order to send mail as Hotmail identify in Gmail, user has to fallback to unsecured connection to port 25 of Windows Live Hotmail SMTP server.

Thus, the solution is to uncheck and untick the Always use a secure connection (SSL) when sending mail setting and make sure SMTP port is 25.

Send As Hotmail Email Address in Gmail without On Behalf Of

Of course, the insecure connection without SSL potentially opens a security vulnerability and leaves much to be desired.


3 Responses to “How To Send Mail As Hotmail (smtp.live.com) in Gmail”

  1. Justin Goldberg
    November 3rd, 2009 22:34
    3

    oh the irony, microsoft’s smtp requires no encryption, but google’s smtp service requires encryption. Guess which one will fare better in the cloud?

  2. Sonny*Daze
    September 6th, 2009 21:51
    2

    The only way to get this & other email clients to work is either:
    1) Get your ISP to “unblock” Port 25 (which they probably won’t. It’s highly used by “Bulk-Spammers”)

    2) Use your ISP SMTP server instead of the *.live.com one

    (AT&T’s is fmailhost.isp.att.net (port # 465)

  3. asdasd
    August 26th, 2009 04:25
    1

    “Of course, the insecure connection without SSL potentially opens a security vulnerability and leaves much to be desired.”

    Nonsense! First of all that’s for the connection between Google and Microsoft (I don’t believe it goes over public hotspots) and second of all Google tries to authenticate using STARTTLS and if it fails does NOT allow that mail server to be added, therefore the SMTP connection is ALWAYS encrypted. Please check for facts before writing such an utter rubbish sentence.

    BTW: Google does not mind receiving mails over unencrypted POP3…

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