Outlook and mail services/ can't send mail to external emails

I have been setting up os x server as a mail server for my company. I bound open directory to active directory but could not manage mail for the active directory users that way, so I started creating new users through open directory.
I've hit a couple snags that I can't quite figure out. First, I can send and receive mail to other open directory accounts fine, but not externally. I've set up my MX records and a name records for my Internet domain.
I can receive emails from an external email address, I.e. Gmail, but cannot send to them. It gets stuck in the mail server's queue. Information logs says operation timed out for smtp.gmail.com and their ip address.
I forwarded the ports, 25, 993, etc from my dsl router to my firewall router, then from there to my mail servers static ip address. I'm at a loss. If it matters, I'm on a residential dsl currently, my ISP claims to block port 25, but in the log it looks like it goes through and sees gmails ip.
Secondly, this is all through the mail.app for my MBP. When I set up outlook 2003 on xp, I can send emails, but it doesn't download any. No errors in either the information log or outlook, outlook says it completed successfully. If it matters, I was getting an error from outlook previously, helo error for not a fqdn, but I deleted a line in the main.cf that required fqdns.
I appreciate any help.

***EDIT*** I have outlook working....now it is just the external email thing. Again...my ISP says they block port 25, but I went into /etc/postmail/master.cf and added to have SMTP go on port 2525 and still no go. Any help would be greatly appreciated!
***END EDIT***
I apologize...here is the SMTP information level log for sending to gmail
Jun 29 16:36:18 ANSENMSG postfix/smtp[17251]: 152CB659FA: to=<***@*******.***>, relay=127.0.0.1[127.0.0.1]:10024, delay=6.3, delays=0.03/0/0/6.3, dsn=2.0.0, status=sent (250 2.0.0 Ok, id=15055-04, from MTA([127.0.0.1]:10025): 250 2.0.0 Ok: queued as 582EA65A09)
Jun 29 16:36:18 ANSENMSG postfix/qmgr[15069]: 152CB659FA: removed
Jun 29 16:36:48 ANSENMSG postfix/smtp[17299]: connect to mail.*******.com[**.***.**.**]:25: Operation timed out

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I had an imap account in my iPad and my iPhone 4. They worked just fine till about Christmas. They act like they are checking the mail and it shows there is mail to come in, but it just goes back to saying checking mail. Can't send mail either.

I had an imap account in my iPad and my iPhone 4. They worked just fine till about Christmas. They act like they are checking the mail and it shows there is mail to come in, but it just goes back to saying checking mail. Can't send mail either.

Update to above question:
Hello All,
To anyone with the same problem described above, on THEIR iPad (if it is running iOS 7.0.2):
Go to Settings; Mail, Contacts, Calendars; DELETE your *******@btinternet.com e-mail account, that you originally set up either using 'Other', or the 'BT' option which I am sure was in the list previous to the iOS 7 update.
Then ADD a NEW account choosing YAHOO from the list of options. DO NOT USE 'OTHER'.
Enter the correct details just as you (almost certainly) had already done in your previous attempts using 'other'.
When you see the 'verifying......' and 'the blue ticks' you should be able to exit settings and open your mail app and then receive all your 'old' e-mails again, AND be able to SEND as well.
All my 'old' e-mails, were NOT found in the 'old e-mail' folder though. THEY are still in my inbox.
So this fix worked for me.
After I deleted my account from 'OTHER' and put it in Yahoo, I like other people also ended up with more folders.
I hope this works for you on YOUR Apple devices.
Bob

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Hi there tamarafromdarien,
You may find the troubleshooting steps for iCloud Mail in the article below helpful.
iCloud: Troubleshooting iCloud Mail
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If you're attaching a large file
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thank you so much

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Can download mail but can not send mail. With parallels on and xp pro I can easily set up outlook to send and receive mail. But no! The great Apple which is supposed to be easy can not send an email with the same settings. So, back to Windows to do what should be easy on a mac. I think that perhaps the new Safari or something messed this up.

If you'd like to approach the problem as something you don't understand, and also something that can be fixed, then you'll probably be able to set up your email account.
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I'm afraid the Great Apple, as you referred to them, is not able or hasn't focused on the ability to automatically set up accounts with every ISP. They appear to have made some assumptions that work with most servers. Who know's, next month the settings or assumptions may work, or Apple may update their setup script to make allowances specific to Time Warner, but since this has been a problem for over 3 years, I wouldn't hold my breath.
Google: leopard mail roadrunner problem = about 96,000 hits of all sorts.
Google: vista email roadrunner problem = about 1,410,000 hits of all sorts.
Google: windows xp email roadrunner problem = 243,000 hits of all sorts.
Looks like Apple's getting it's market share of problems with RoadRunner and Time Warner
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Outlook and mail services/ can't send mail to external emails

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