Guys, I really need some assistance here. I've been at it for hours but I can't for the life of me figure this one out.

I have a client with a business, and we recently set her and her two employees up with a hosted exchange service. The two employees were easy to set up and have had no problems that I know of, but my client's setup is not working.

She has a desktop with XP and Outlook 2007. The setup process went fine, and she can work in Outlook just fine for about 10 minutes. After that, something happens with the connection between Outlook and the Exchange server and it won't come back unless you exit the application, sometimes having to end the task.

Symptoms:

- when it's getting close to the time where it quits, the system tray icon starts flashing for split-seconds, as does the message that "all folders are up to date." I don't know what it's flashing to because it goes so quick.

- about a minute before everything comes down, I'll get a message that "Connection to Microsoft Exchange has been restored." The message that it went down either comes to fast or not at all. At this point I can usually still send and receive emails.

- then, inevitably, I'll get the message "Microsoft Office Outlook is requesting data from the server" and it will sit like that with an hourglass over the system tray icon until I close the application.

- her iPhone is set up with this Exchange server and doesn't have any of these issues.

Those, sadly, are my only symptoms. It's been a VERY annoying issue to fix because it takes so long to test if it's still happening. Here's what I've tried so far:

- disabled all Outlook add-ins
- repaired Office
- reinstalled Office
- repaired the network connection
- uninstalled and reinstalled network adapters
- replaced the router
- set up Exchange account on client's laptop and experienced the same problems
- took laptop to Starbucks, but found it difficult to test if the problem was still happening there. I might try taking it home next.
- quadruple-checked the settings received from the Exchange provider


I'm in a big bind here, folks. My client is extremely busy, and lives by her email. She could be a great client for me in the future and refer me to others, but I really need to help her out here first!

I can't provide any specifics (because thankfully I have no access to Outlook or Exchange these days), but some things to consider:

Outlook and Exchange are built around the idea that both the client and server live on the same LAN. Keeping Outlook in it's default mode is likely bad if they are using a hosted Exchange service across the internet. This method of accessing the server is usually called MAPI.

Outlook does have an "offline" mode and can cache the server info, allowing a user in an office to take a laptop home, and keep access to any previously downloaded e-mail. I want to say this is also referred to cached mode as well. Based on the popups about access being restored, it sounds like this mode might be active.

Outlook also has a setting somewhere to talk to the Exchange server using the ActiveSync protocol. This is a Webdav protocol using HTTP, instead of MAPI, and is how the iPhone is accessing the server. This is probably the best way for Outlook to also be configured, since the server is not on the customers LAN.

Odds are, the tray icon is momentarily flashing messages about connectivity issues, since MAPI isn't really built to traverse the internet. We saw similar issues at my previous job when the Exchange server was moved offsite and into a datacenter that had some initial bandwidth issues.

Thanks for the response, Tom. All of what you said is true, though I'm pretty sure that Outlook is set up to access the server over HTTP. At least, that's what I get from the instructions I followed that were given to me by the company hosting the email.

Here's a question: before I moved the client to this new host, she had amassed a mailbox well over the advised 2GB limit. Not the biggest I've seen, but at least 2.8GB. I didn't notice this until I'd backed up her data and then uploaded it to the new servers. I then worked with her to get it down to around 1.5GB (mostly by deleting thousands of sent items).

Could the contents of her mailbox cause the problem? I'm trying to figure out why her account is causing problems when her employees, who have FAR less data, don't seem to have any issues with the same service.

I've asked her to try using her laptop for the time being, and to try taking it somewhere with WiFi access. She's going to get back to me with the results.

Yes. Outlook can and does wig out when its .ost and .pst files are, or ever have been, too big.

I'm just wondering if it's still the issue, though. She's been at 1.5GB for the week now.

Do you think it would help to back up whatever she has into a new PST file on her machine, make sure it's all nice and compressed, have the host wipe out her account, and start fresh? I'd imagine it couldn't hurt...

I'm gonna go with Mark on this one (even though he hasn't weighed in yet) and say "switch to linux". :P

Do her a real favor and switch her to hosted Google apps?

Matthew

That would certainly have been my choice. It would have been cheaper, too. This company is charging $25/month for unlimited storage for all users, or $15/month for something like 2GB total for all mailboxes. Google Apps would have been better for a three-person company (at $50/user/year), but honestly the calendar and contact syncing isn't quite there yet for Outlook, and I keep running into people who are obsessed with continuing to use Outlook.

When this Exchange stuff works correctly, it's fantastic. Between the three users in this company, there's an iPhone, Android device, and a Blackberry. The first two were a breeze to set up and took about two minutes before everything started syncing perfectly. The Blackberry, on the other hand, is a PITA. The user is going to have to upgrade her $30/month plan to a $45/month plan in order to be put on a BES instead of a BIS, and the configuration process is a bit more complicated. Plus, the user only has contacts in her phone, and doesn't want to sync it with Blackberry Desktop. So I don't know if setting her up for the BES will wipe out all her current contacts, sync them up to the Exchange server, or do nothing with them. I'll just back them up to my laptop first and go from there, but still, the Android and iOS processes were cake compared to the stupid Blackberry. I always forget how much I despise that interface...

Why not Office Live? We get Live@Edu free here at the college to host our Student E-Mail. I have no idea what it costs for business, but it's worlds above Google Apps. You can connect Outlook clients, phones etc.. to it no problem so it would basically be no change in functionality.

Because Exchange and Outlook suck universally.

What's the alternative IMAP and Google Calendaring?

Sure.

Honestly, the Post Office and a desk calendar would be better.

Ok back to the originial question... When the connection dies try this trick- right-click on the Outlook System Tray Icon (by the clock) and get Connection Status. That will at least tell you what kind of connection it's using if it still exists. Actually view the Connection Status before it crashes as well. If it's connecting using HTTP/RPC there could be issues there. You might try turning off RPC over HTTP if you can (AKA "Outlook Anywhere" in the Connection tab of Account Settings.

Thanks so much for the idea. I'll look for that.

Weirdly, I spoke with the client the next evening, and she said she'd been having no email problems. I'm not sure why, since at the point I left the only progress I'd made was to get a repeatable failure (open Outlook for 10 minutes, and without fail the connection would die). But perhaps one of the 30+ things I tried on Friday actually worked and just needed a little time to get the kinks ironed out. I don't know, but it's one of those times where I'm going to be happy with the results and not tinker with it at all just to figure out what the cause was I'll deal with it if it comes back.

Thanks for the help, though. I was a little panicked because this will be an important client for me, and I think she's happy so that's good.

Because Google has proven then can provide the service at scale reliably, has an extremely optimized web interface, and provides activesync for email, calendar and contacts.

Read the story about how Google recovered emails from tape when an upgrade went awry. Then look at what happened when the sidekick servers crashed.

According to Microsoft all the sidekick data was recovered.

http://news.bbc.co.uk/1/hi/technology/8309218.stm

And Microsoft hasn't? There are literally millions of student e-mail accounts on Live@Edu and probably hundreds, if not thousands, of schools using it. Microsoft is using there tried and true "inflitrate Colleges/Universitites by giving huge discounts" (in this case free) strategy to push their online services and guess what.. it's working.