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Quick Tips: Troubleshooting Outlook connectivity

Introducing Quick Tips: helpful tips from our Support and Product experts for getting the most out of your cloud services. Each installment of our series will tackle a different topic, from troubleshooting a issue to discovering helpful features and functionality that can make your work life easier.

In this installment of our Quick Tips series, Phill Lewis discusses ways to resolve Outlook connectivity issues. They don’t happen often, but they can be frustrating when they do occur. Here are some things to try to resolve the problem.

What to do when mail takes a long time to send or just isn’t coming in

Here’s the scenario: You open your Outlook mail app, and the Outlook status bar is showing “Connected to Microsoft Exchange” or “Connected”, but your mailbox doesn’t appear to be syncing properly. Or, sometimes, you might see a status of “Trying to connect…” or “Disconnected status”.

1. Check your Working Offline setting

At Intermedia we have a few standard procedures which often resolve these issues. I’ll start off with the easy ones first.

First, check your Work Offline setting in Outlook to see if that’s turned on by mistake.

2. Check things in OWA

Was your password changed recently? If Outlook is set to remember your password it may not have prompted you to enter your new one yet, or perhaps the window prompting you is buried deep behind other windows. Trying logging in to the Outlook Web App at owa.intermedia.net

If you can log into OWA, then you’ll want to go back and close the Outlook app. Then you can open it and your new password will be remembered.

If you cannot log in to OWA, you may see a couple of different error messages that will require a couple more steps to fix:

  1. If you see “Login or password incorrect”, contact your administrator to reset your password and help you check that you have the right one set in Outlook.
  2. If you see “Server is unavailable,” clear the browser cache, make sure you are connected to the web, and try to log in to OWA again. You can also try using a different browser.

3. Focus on the ISP

One of the first inquiries I make, if those two actions don’t solve the issue, is to check if the local ISP is Comcast. The strange thing with Comcast is that other Internet traffic will be completely unaffected even when email isn’t syncing, making this a tricky problem to spot.

Some modems that Comcast gives to Business Class customers have both Firewall Protection and Gateway Smart Packet Detection enabled. Secure traffic, such as the HTTPS used by Exchange, will stop working as soon as the Smart Packet Detection identifies this specific type of traffic.

Additionally, the modem firewall combined with antivirus protection on a user’s computer can cause a double firewall condition that may also affect performance.

The solution is to turn off both Firewall Protection and Gateway Smart Packet Detection on the Comcast modem.

4. Reset the cached mode setting

Not using Comcast? For other ISPs, and even in the case of Comcast where the modem problem is resolved, there are other things to check.

Try “turning it off and on again”. For Outlook, that means Enabling/Disabling cached mode. Cached mode is good as it provides faster performance, but on rare occasions in older Outlook versions it needs to be turned off and back on. Here’s how:

Go to File (or Tools on a Mac) > Account Settings (or Accounts on a Mac). Now, double-click on Exchange email address and uncheck Use Cached Exchange Mode. Save the changes and restart Outlook. This can then be repeated to turn cached mode back on to keep you at peak performance.

5. Try opening Outlook in Safe Mode

Sometimes new add-ins to Outlook (Windows version only) can create unexpected difficulties. You can start Outlook in its default start up mode without any add-ins by starting Outlook in Safe Mode. It’s easier than it sounds:

  1. Shut down Outlook, if you haven’t already.
  2. In Windows, go to the Start menu and in the search box, type: outlook.exe /safe

If Outlook starts running better, you can start each new add-in and see if one is being particularly troublesome. Then you can remove it.

  1. In Outlook 2010/2013, go to File > Options > Add-Ons.
  2. In the Manage field, choose COM add-ins and then select Go and highlight an add-in and click Remove.

We’re always here for you, 24/7

If these tips don’t work out, don’t worry. You can always call our Support team 24/7 at 800-379-7729. Before you call, we recommend that you gather some information. That way, we’ll be able to help you much faster.

1. Run a trace route

The first thing to check will be if there is any trouble between your computer and our datacenter. A trace route will show the route your computer takes to talk to us. This is going to look complicated, but it’s only a bit of copy-and-paste, then running the command, and then gathering the results.

  1. Go to Start > Run.
  2. Type cmd and press Enter.
  3. This will bring up a command prompt window. It has a line that looks like this:
    C:\Documents and Settings\jsmith> _

The next step is to determine where you connect to our Exchange environment to tell the trace where to go. There are two ways to get this information:

  1. Back in Outlook, you’ll need to check the account settings: Go to File (Tools in older versions) > Account Settings and double-click on your Exchange email address. Now select More Settings > Connection > Exchange Proxy Settings and there you’ll find a server name that you’ll want to copy.
  2. OR, log in to OWA and look at the URL that appears when your mailbox opens. It will be the content that appears between “https://” and “/owa”.
  1. Back in the command prompt window type tracert, then paste the server name from Outlook (or OWA), and hit Enter. The command runs, and it will look a bit like this:

The higher times show where the trace takes longer to get to Exchange and the longer Outlook takes to communicate. The starred lines indicate a very long wait – so long that it timed out. Sometimes this will show a problem on the local network on the route you take to get to the web or other times it will indicate a particular bottleneck at an ISP. You’ll want to keep this command prompt window open when you call us.

2. Find your CAS

One other piece of information that will help our Support team diagnose the issue is your Client Access Server, or CAS. The CAS will act as the real destination for OWA – if you used OWA to find your server when you ran the trace route, you noticed that after you logged in, the address bar changed to the mailbox’s Exchange domain. 

To find your CAS, you’ll want to substitute your server name that you found when you ran the trace route into a special URL and then open that URL. If you’re using our Exchange 2010 service, take that server name and paste it into https://your-proxy-address/server.aspx in place of the “your-proxy-address” part of the URL. For Exchange 2013, paste it into https://your-proxy-address/scripts/server.aspx

If you don’t know which service you have, try both! When you click to open that URL, you’ll see something like this:

 

We will use this information to see if we have a problem with a specific domain (180 in this example) in our environment or with a specific CAS server.

Here are some other pieces of information that will help us diagnose and fix the issue:

  1. Whether there is a problem sending and receiving in OWA
  2. Whether Outlook behaves differently in regular vs Safe Mode
  3. The version of Outlook (go to Help > About) and version of Windows you are using
  4. Your public IP address (try MX Toolbox: http://mxtoolbox.com/WhatIsMyIP/)

We’ll use all of this information to get your email functioning properly. And of course, we’ll be happy to answer any other questions you have.

About Phillip Lewis

Phillip Lewis works on the Onboarding team. He spends his time transporting client data to Intermedia’s systems. His background is in British digital technology and its culture. In his spare time he likes to paint model airplanes.