Move to 353 - Firewall Issues

Posted on 2013-06-23
Medium Priority
Last Modified: 2013-06-25
Existing Site:
SBS 2003 Server XXX.local is the domain and they bring mail into them for their XXX.com domain, there is also a small 2nd business in the company called YYY and the same SBS server also brings in mail for YYY.com. (All users in same office using same server and broadband)
YYY would like to separate its mail from the XXX Server but would like to keep using the SBS server to share files with XXX.
I got them to purchase Microsoft 353 hosted mail and I setup YYY.com on it last week, I configured the mail accounts in 365 for the 3 YYY users and got the IPS to setup the mx records and the dns settings.
I was on another site when the dns settings were completed so I did a test setup in Outlook 2007 of one of their accounts on my own laptop and the autodiscover worked and mail setup perfectly.
I then used logmein to connect into the laptop of one of the YYY users and setup a 2nd mail profile on his laptop for the YYY.com mail and the autodiscover did not work, it kept asking for the username and password, I then tried to manually setup the account using the settings from my laptop that were created but again it kept asking for the username and password.
I am wondering if the sonicwall onsite for the XXX.local domain is blocking the 365 mail ?
There are rules on the sonicwall -see below
1)      Port 25 Allow Mail in from Postini IP range to SBS server ALLOW (Allows in mail for XXX and YYY.com but only from Postini)
2)      Port 25 Mail Allow in from Postini Backup IP range to SBS server ALLOW ALLOW (Allows in mail for XXX and YYY.com but only from Postini)
3)      Port 80 Allow WAN to LAN SBS Server – for OWA and iPhone I think
4)      Port 443 Allow WAN to LAN SBS Server – for OWA and iPhone
5)      LAN to WAN * - Allow
6)      WAN to LAN * - Deny

Or do I need to remove YYY in the XXX.local exchange manager?

I will be onsite in a day or two again so any tips would be great.

Question by:MidComp
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LVL 46

Accepted Solution

Vasil Michev (MVP) earned 2000 total points
ID: 39269699
I am assuming you have waited for propagation of the DNS and run the Office 365 desktop setup on the machines? You need some updates for Outlook to work with Office 365 and the desktop setup will install them for you.

Also, run the Test E-Mail Auto-config wizard on that machine and see what server it comes up with. Or simply look at the prompt, it should display a server name.  If it is not something.outlook.com they you have a problem :)

You can review the list of IPs for O365 and Exchange Online here:


Author Comment

ID: 39269737
Yes I have waited on the DNS to propagate and the Microsoft 365 site site showed them as fine.
I installed sp3 for outlook 2007 - is there more updates needed ?

I ran the test email auto config and it shows no issues at all when ran on the users laptop.

I never ran the 365 desktop setup so I will give that a try.
LVL 46

Expert Comment

by:Vasil Michev (MVP)
ID: 39269751

Author Comment

ID: 39269761
Perfect will try those and come back.

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