Hi, first post so I hope I'm doing this right. So I was setting up my fresh install of Mountian Lion - spent all of last night getting everything updated - and I decided to get my email synced. I set up my Google account in the "mail, contacts, and calendars" tab in system settings, and quickly realized there was a problem when nothing would send. I receive email just fine, however. I checked my smtp settings and no matter how I altered the port settings (connecting individually to 25, 465, and 587), the SSL checkbox, or reset the whole gmail account connection, the outgoing smtp server would not simply connect. Specifically, the error I receive in the connection doctor reads "Could not connect to SMTP server, check your network settings... Account preferences, SSL... etc." After trying this over and over again, I decided I'd try to send something from my iPhone 5 - which is connected to the same Gmail account. Now, I receive the errer "Cannot Send Mail: The connection to the outgoing server "p14-smtp.mail.me.com" failed. Additional Outgoing Mail Servers can be configured in Settings > Mail, Contacts, Calendars." Some more information regarding my mac: White macbook (2 gb, intel core 2 duo), I've enabled iCloud (I suspect the issue revolves around this?), I'm running 10.8.3. Thanks for taking the time to read and help me with my problem!