MAC in Win environment - Can't send external mail

[vanillawafer]

Hello,

I have a Mac on my Windows network. I have no idea how anything is set up. Everything was working fine until the Exchange server went south on us a few weeks ago. Basically as it stands now, my Mac user can't send any mail out externally. At one point, I couldn't either, however after upgrading to office XP I am fine now. He's able to send internally and receive mail from others. Initially I had to add him to the WINGATE server to get to the internet. There is a possibility that he's changed his password or something lately. I know none of this makes any sense, it doesn't make any sense to me either. Please help.

 

[blubomber]

What version of Mac OS is it? What is the Mac user using for email? what version of Exchange is your company on?

 

[vanillawafer]

Our company is using exchange 5.5. The user is accessing mail through Microsoft Entourage SR1, if that makes any sense. His OS is 9.2.

I did check his TCP/IP settings and basically the only thing that missing is where the router address is. We have never had anything in that space, however, I just remembered that we recently installed a firewall.

Do you think that the firewall has something to do with it? Should the firewall settings be put in where it ask for TCP/IP settings?

Also, we have gator blocked out of the firewall. He has his password set up to automatically log on. I am thinking that it may view that as being gator, but I don't know.

Any suggestions?

 

[jimoblak]

I just remembered that we recently installed a firewall

Is the firewall blocking the outgoing mail port? Many firewalls block port 25, especially in the climate of email worms.

- - picklefish - -

Why is everyone in this forum responding to me as picklefish?

 

[blubomber]

First off, i would like to suggest using Outlook 2001 for you mac user. From what i have read, and i may be wrong, Entourage does not connect directly to an Exchange 5.5 server, only Exchange 2000 and 2003. Outlook 2001 can see the Exchange server and knows it is an exchange server, Entourage just sees it as a mail server. I am not sure if i explained that good or not.

Where is your firewall located? Is it between your exchanger server and the internet? What about your windows users? Can they send mail to the outside? Are your windows users using outlook?

If your windows users can send out side email using outlook connected to the exchange server, then the problem could be the Entourage setup.

 

[vanillawafer]

Everyone can send out except him. As I stated I couldn't send out before but I am not using MAC. I have since upgraded in XP and hanven't had any problems since.

Do you think that I should put a setting where the router settings are blank in the mail settings dialog?

 

[blubomber]

Yes i would try that. I did forget to mention that Outlook 2001 is free!! i had recently setup Outlook 2001 to connect to my company's exchage 5.5 server on a new Mac running OS X. You can download it from the Mactopia area of Microsoft's website. i dont know if your Mac user can make the chage, but it would be something to concider and i think help make your job easier.

 

[OldPhoneGuy]

I just checked Microsoft's web site and it says that if the Mac is running OS9 and you use and Exchange server the Mac should use Outlook 2001.

 

[vanillawafer]

I have tried everything. One more interesting thing now he can't map to any networked drives. He's still receiving external mail, but not able to send any.

 

[blubomber]

Are you using Active Directory on your windows network?

Also, did his password expire for the account he uses to access the windows shared data?

 

[vanillawafer]

I am using AD, and as I stated in the the beg. there may be a possibility of him changing his password. I have no idea what to do next.

 

[vanillawafer]

Well, he still can't send any external mail. In addition, he can't map to any networked drives. Does anyone think that the drive mapping issue and him not being able to sent externally are the same issue?

I seem to think that there are two separate issues, but I may be wrong.

 

[blubomber]

Does he have an AD account to gain access to the shares? Try having him log into a windows workstation using his AD account. I am assuming he has one so that he can get access to the shared folders on you windows network.

As far as email, have you looked into using outlook 2001? To me it almost sounds like a security issue and he is not authenticating correctly to your windows network.

 

[vanillawafer]

He does have an AD account set up. We did try to download outlook 2001, but it can't see our Exchange Server. I think that it's a combination of issues here. I think that the issues with him not being able to map to any drives may have something to do with why we can't send externally. Security? Yes, however, I can't seem to figure anything out. The only thing that changed is that we installed a firewall, and as far as I know, there is nothing blocking blocking email ports. Like I said, he is still receiving mail as usual, it's just sending it out externally.