Exchange External Connectivity Issues

I'm having connection issues with my Exchange Server from outside of our network.

Internally everything works fine. We can send / receive emails and access Outlook Anywhere without any issues. Externally though we have major stability / connectivity issues.

Attempting to access outlook anywhere is working hit and miss with no obvious reasons. When in connects it works fine so it wouldn't seem to be port / firewall settings. When it doesn't work it just tries to connect before failing with a page is not available message no matter what the browser or machine.

The outlook client which works fine internally struggles to connect externally but again will do it so again it seems not to be port or setting issues.

As the machine works fine internally I'm fairly sure there is no hardware issues. As it works sometimes I'm assuming its connectivity somewhere - but looking for how to test.

The system has been working fine for many years and only recently started playing up. Nothing has changed on the server settings or firewall.

A traceroute to the server does show lots of timeouts but not sure if that helps.

1         0         0         0           
2         32         32         32           
3         32         32         34           
4         32         34         32         
5         32         32         32             
6         32         32         32           
7         35         35         35             
8         39         39         39           
9         184         183         183
10         182         183         183           
11         179         179         179           
12         179         179         179             
13         180         179         179           
14         179         Timed out         Timed out           
15         179         Timed out         Timed out           
16         260         193         Timed out           
17         Timed out         Timed out         196       
18         Timed out         Timed out         Timed out                    -  
19         Timed out         Timed out         Timed out                    -  
20         Timed out         Timed out         Timed out                    -  
21         Timed out         Timed out         Timed out                    -  
Trace aborted.
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Imtiaz HashamTechnical Director / IT ConsultantCommented:
a. are you having internet issues?
b. For trace route to work, some router might block it
c. Is your firewall set to allow traffic to be NATted to the Exchange Server
d. Have you tested your system using
e. Have you run the Best Practice Analyser?

Let's start with the first question - browsing the internet.

And one of the other things I would look at is just to ensure your ISP is not throttling traffic on the particular port.

Use just to ensure that your ports are open fine :)

Let me know how you get on.
EmendearAuthor Commented:
Thanks for the reply. Much appreciated.

a) No internet issues not any other service problems that I can see. We have other services running that all seem to be working fine (like ftp and other websites, remote vpn access etc) and no-one has been reporting any other issues.

b) The trace was a hail mary :) Just trying to provide as much information as I could.

c) Yes - and when Exchange DOES connect it works fine. I can send and receive emails etc perfectly, Same as with OWA access - it's just the intermittent connection issues that is the issue.

d) I'm running through them now the issue being is I'm getting fails on some tests which are due to the connection issue. For example while testing Outlook Anywhere it is saying port 443 A network error occurred while communicating with the remote host yet 30 seconds later I can open a browser and run OWA which means the port has to be open and then if lucky I can re-run the test and it gives a different response saying the port was opened successfully. It's just hit and miss.

e) I haven't run yet but it's on the list. As the machine "technically" hasn't been changed for years nothing here should have changed but I'm open to any option atm.

I have my ISP looking at the issue as well but of course that comes with it's own level of pain. Again nothing "should" have changed and the router / firewall is managed by them as part of our business setup so it certainly shouldn't be.

Canyouseeme is reporting errors on all ports ... but assuming that is just firewall settings not allowing a response as again when the system does work it works fine.

I guess the main frustration is that it's intermittent. My logic says that if it works when it works then the setup "should" be OK but of course logic and IT don't always go hand in hand.
Imtiaz HashamTechnical Director / IT ConsultantCommented:
I totally agree with your last comment:

"of course logic and IT don't always go hand in hand"

Back to the question at hand.  based on your latest information, the issue is with the routing level.  As it's a managed router, I'd ask the ISP to look into it asap.  And I totally understand the headache part.

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