Travel Technology - VPN Connects, but not Outlook

There is one hotel I stay at regularly (Marriott Courtyard in Edmonton, AB) that gives me some minor grief related to connectivity.

I am able to connect to their network (wired), and establish my company VPN. I am even able to then Remote Desktop to several company servers.

What I cannot seem to do is have Outlook connect successfully. Outlook starts, but never connects. It just tries continuously and eventually gives up, until about 5 minutes later, tries again, etc. I end up using my company's web mail, which works but is inferior to Outlook.

Is there some specific port than Outlook needs that is being blocked by the Courtyard? Is there a legitimate reason for the hotel network to block that port?

I am looking for specifics to tell the hotel network people. The desk/customer service never seem to know what I'm talking about...

There is one hotel is stay at regularly (Marriott Courtyard in Edmonton, AB) that gives me some minor grief related to connectivity.

I am able to connect to their network (wired), and establish my company VPN. I am even able to then Remote Desktop to several company servers.

What I cannot seem to do is have Outlook connect successfully. Outlook starts, but never connects. It just tries continuously and eventually gives up, until about 5 minutes later, tries again, etc. I end up using my company's web mail, which works but is inferior to Outlook.

Is there some specific port than Outlook needs that is being blocked by the Courtyard? Is there a legitimate reason for the hotel network to block that port?

I am looking for specifics to tell the hotel network people. The desk/customer service never seem to know what I'm talking about...


Well SMTP works on port 25, but if you can VPN in then that doesn't make a difference.

Is there some specific port than Outlook needs that is being blocked by the Courtyard? Is there a legitimate reason for the hotel network to block that port?
Let me amplify "amp." Once you have VPN'd into the company, all traffic to the company is carried over an encrypted tunnel. The hotel would has no visibility inside of this tunnel. Assuming your mail server is inside of your company's network, Courtyard can't see it.

HOWEVER. You might have split tunnel enabled and/or for some weird reason, maybe the mail server isn't hosted at your company, or within the space of the VPN. To test this, we have to know more about your mail setup. Is your outlook account setup for POP, IMAP, or Exchange?

Let me amplify "amp." Once you have VPN'd into the company, all traffic to the company is carried over an encrypted tunnel. The hotel would has no visibility inside of this tunnel. Assuming your mail server is inside of your company's network, Courtyard can't see it.

This was also my understanding of how VPNs are supposed to behave. Yet consistently at only this one hotel, my Outlook never connects.

HOWEVER. You might have split tunnel enabled and/or for some weird reason, maybe the mail server isn't hosted at your company, or within the space of the VPN. To test this, we have to know more about your mail setup. Is your outlook account setup for POP, IMAP, or Exchange?

Exchange.

I had this problem. I was able to get to some servers but not all of them and definitely not the mail server.

My network guy said this sometimes happens in hotels because the server name, for some reason, is not recognized. Poor guy spent over an hour trying to get me fully connected.

I changed my links to the IP address and was able to access all my servers. I was never able to get mail, even though we tried to perform surgery on the access for it, which included changing some files.

I had to use webmail also.

With my company VPN (using Racom RVI), in some situations the VPN seems to partially connect, giving the symptoms you describe. What I've been told to do (and it works) is to simply log into the VPN twice in a row.

My system allows either logging into the VPN as part of the boot process (if plugged in) or after the OS it up. In a place with problems (most hotels, airports etc) I wait until after the OS is up, run the VPN log in, wait a minute, then run the VPN ap again and re-login. (similar to what you would do if it timed out). Why this works I can't tell you - and my company IT says "that's weird"...but it works.

In fact, I've done exactly that this morning. I'm in a hotel in Dallas... Also weird is that I never have to do this at home - even using Comcast.

RFT :)

That's fairly common for us, putting the IP address of the Exchange server (the internal one) in the local hosts file fixes it all the time.

For some reason the VPN doesn't translate all the internal addresses (10 dots) for us and the servers can't always be found, so we need to have it in the hosts file.

Of course, we don't need it all the time, so it's fairly random when as to when it happens, but it's always in another time zone at some weird hotel connection. I just add in all the entries to everybody now.

Hopefully that is the issue, try pinging the exchange server without it's IP address in the hosts file once you are connected to see if it's resolving correctly, if not you need an entry for it.

Hopefully that is the issue, try pinging the exchange server without it's IP address in the hosts file once you are connected to see if it's resolving correctly, if not you need an entry for it.This is exactly what my IT guy had me do, and it didn't work 100%, but after figuring out what we had to do to get me to all the other resources I needed, I just thanked him and used webmail. I should play with it and convert everything on my laptop to IP addresses so I don't have to deal with it in the future because I'm sure the next time it happens, it will be when I urgently need to get in and don't have the time to play with settings.

Sometimes it is a port 25 issue; you can try setting your SMTP port to 587. I've found that helpful in a few Marriotts.