Gmail outgoing server issues with Apple Mail

Hi,
I'm currently running OS X 10.8.5 Mountain Lion, and trying to set up my gmail account in Apple Mail. I can recieve mail just fine, but am not able to send mail. for the outgoing server i typed "smtp.gmail.com." When i look at the Mail Connection Doctor it says that the imap incoming was able to login in and connect, as well as the smtp is succeeding with its connection to the server. However I keep getting the message that says "cannot send message using the server smtp.gmail.com"
With the connection doctor window still up, upon trying to send my letter again, an error comes up...even though the connections are still good. The error reads:
INITIATING CONNECTION May 09 13:56:22.639  -- host:smtp.gmail.com -- port:587 -- socket:0x0 -- thread:0x7fa9146888b0
CONNECTED May 09 13:56:22.755 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:587 -- socket:0x7fa915b0bec0 -- thread:0x7fa9146888b0
READ May 09 13:56:22.785 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:587 -- socket:0x7fa915b0bec0 -- thread:0x7fa9146888b0
220 mx.google.com ESMTP b8sm443235igx.3 - gsmtp
WROTE May 09 13:56:22.797 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:587 -- socket:0x7fa915b0bec0 -- thread:0x7fa9146888b0
EHLO [192.168.1.149]
READ May 09 13:56:22.830 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:587 -- socket:0x7fa915b0bec0 -- thread:0x7fa9146888b0
250-mx.google.com at your service, [162.17.148.217]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
250-ENHANCEDSTATUSCODES
250-PIPELINING
250 CHUNKING
WROTE May 09 13:56:22.835 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:587 -- socket:0x7fa915b0bec0 -- thread:0x7fa9146888b0
STARTTLS
READ May 09 13:56:22.868 [kCFStreamSocketSecurityLevelNone]  -- host:smtp.gmail.com -- port:587 -- socket:0x7fa915b0bec0 -- thread:0x7fa9146888b0
220 2.0.0 Ready to start TLS
WROTE May 09 13:56:23.039 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:smtp.gmail.com -- port:587 -- socket:0x7fa915b0bec0 -- thread:0x7fa9146888b0
EHLO [192.168.1.149]
READ May 09 13:56:23.069 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:smtp.gmail.com -- port:587 -- socket:0x7fa915b0bec0 -- thread:0x7fa9146888b0
250-mx.google.com at your service, [162.17.148.217]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH XOAUTH2 PLAIN-CLIENTTOKEN
250-ENHANCEDSTATUSCODES
250-PIPELINING
250 CHUNKING
WROTE May 09 13:56:23.073 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:smtp.gmail.com -- port:587 -- socket:0x7fa915b0bec0 -- thread:0x7fa9146888b0
MAIL FROM:<[email protected]>
READ May 09 13:56:23.105 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:smtp.gmail.com -- port:587 -- socket:0x7fa915b0bec0 -- thread:0x7fa9146888b0
530-5.5.1 Authentication Required. Learn more at
530 5.5.1 http://support.google.com/mail/bin/answer.py?answer=14257 b8sm443235igx.3 - gsmtp
WROTE May 09 13:56:23.109 [kCFStreamSocketSecurityLevelTLSv1SSLv3]  -- host:smtp.gmail.com -- port:587 -- socket:0x7fa915b0bec0 -- thread:0x7fa9146888b0
QUIT
If anybody knows what the problem is or how to fix it, I'd be greatly appreciative. In addition, I do have this account being fed to my phone, to which it can send/receive mail just fine.
Thanks

By default Mail should enter all the correct setting for Gmail.
It's asking for authentication.
Select to Edit SMTP settings.
Select your Gmail account from the list.
Click on Advanced.
√ Use Secure Sockets Layer (SSL)
Gmail likes port 465 but Apple default to all ports.
Make sure your password is entered.
Use the Connection doctor to test your settings. You should see green lights to show your receiving and sending settings are correct. Click on Show Details if you see a red light.

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