It’s easier to explain with a picture, but I couldn’t quickly find one.

So, Ootw breaks some typical rules that you might expect to see from a 
traditional web app. For example, even when the user isn’t doing anything, 
every now and again, Ootw communicates with the Exchange server. This allows it 
to notify you when you have new email or when email was deleted on another 
device, etc. Lots of apps do this (e.g., Gmail does it too). It doesn’t do this 
by closing and re-opening a port every time, it keeps a port open and just 
“trickles” data back and forth. (This requires HTTP/1.1 or HTTP/2.0 by the way, 
doesn’t work on HTTP/1.0.)

If the port is force-closed, that is an error, as far as Ootw is concerned. 
Depending on “everything else” (i.e., ADFS, Exchange Federation, is the 
Exchange connection being proxied across datacenters, etc.) the browser and 
Ootw will react slightly different ways. But you’ll generally end up with a 
browser pop and you might also get an authentication pop.

After a certain period of inactivity, Ootw will close that port, to reduce the 
likelihood of port exhaustion on the CAS. I thought that was 2 hours, but if 
you are working with upping your port timeout to 60 minutes, then it’s 
obviously more than 15 minutes and less than or equal to 60 minutes. (And it 
may be different on-premises vs. in the service. I didn’t check.)

From: listsad...@lists.myitforum.com [mailto:listsad...@lists.myitforum.com] On 
Behalf Of Jonathan Raper
Sent: Tuesday, August 23, 2016 9:00 PM
To: exchange@lists.myitforum.com
Subject: [Exchange] RE: Speaking of Outlook Web App

As a followup….

I increased the idle timeout from 15 minutes to 60 minutes for Outlook on the 
Web in O365.

All problems ceased for the end users who were affected.

Very interesting.

I’d love some more detail behind it, but at the end of the day I guess it does 
not matter.

Thanks,

Jonathan
From: listsad...@lists.myitforum.com<mailto:listsad...@lists.myitforum.com> 
[mailto:listsad...@lists.myitforum.com] On Behalf Of Michael B. Smith
Sent: Saturday, July 16, 2016 8:26 PM
To: exchange@lists.myitforum.com<mailto:exchange@lists.myitforum.com>
Subject: [Exchange] RE: Speaking of Outlook Web App

I don’t have time to chase it down right now, but the general recommendation is 
120 minutes or more.

In regards to supporting different timeouts – you’d have to enforce that in the 
firewall. I’m sure that Checkpoint, Cisco, and F5 can support policies of that 
type. I can’t speak to any other vendor.

From: listsad...@lists.myitforum.com<mailto:listsad...@lists.myitforum.com> 
[mailto:listsad...@lists.myitforum.com] On Behalf Of Jonathan Raper
Sent: Friday, July 15, 2016 8:30 PM
To: exchange@lists.myitforum.com<mailto:exchange@lists.myitforum.com>
Subject: [Exchange] RE: Speaking of Outlook Web App

Thanks Michael,

I’ve seen stranger (taking a picture in an electronic procedural record system 
causing a Cisco ASA to reboot!), so thanks for the idea – something for us to 
look at.

One thing that we are considering a possibility is that we changed the idle 
timeout from the default of 6 hours down to 15 minutes in order to fall in line 
with our security policy. The complaints started after that, but not 
immediately enough that I see a definite correlation – when I asked how long it 
had been going on, they said, “about a  month”, which roughly coincides with 
the change.

I’m considering increasing the idle timeout to 30 minutes to see if the pattern 
changes.

Related question – do you know if it is possible to have a different idle 
timeout for a subset of users, or is that a purely global configuration?

Thanks,

Jonathan

From: listsad...@lists.myitforum.com<mailto:listsad...@lists.myitforum.com> 
[mailto:listsad...@lists.myitforum.com] On Behalf Of Michael B. Smith
Sent: Friday, July 15, 2016 4:07 PM
To: exchange@lists.myitforum.com<mailto:exchange@lists.myitforum.com>
Subject: [Exchange] RE: Speaking of Outlook Web App

I’ve never seen this before. It sounds to me like a TCP port timeout in a 
firewall is set too low (just a SWAG).

From: listsad...@lists.myitforum.com<mailto:listsad...@lists.myitforum.com> 
[mailto:listsad...@lists.myitforum.com] On Behalf Of Jonathan Raper
Sent: Friday, July 15, 2016 1:37 PM
To: exchange@lists.myitforum.com<mailto:exchange@lists.myitforum.com>
Subject: [Exchange] RE: Speaking of Outlook Web App

Beuller? Anyone?

Thanks,

Jonathan
From: listsad...@lists.myitforum.com<mailto:listsad...@lists.myitforum.com> 
[mailto:listsad...@lists.myitforum.com] On Behalf Of Jonathan Raper
Sent: Tuesday, July 12, 2016 9:30 PM
To: exchange@lists.myitforum.com<mailto:exchange@lists.myitforum.com>
Subject: [Exchange] Speaking of Outlook Web App

We’re running O365, and have a handful of users who exclusively use Outlook on 
the Web.

They have been complaining of the session “reloading” seemingly at random, and 
even the window taking precedence when it is in the background. In other words, 
they could be typing something in a linux shell and then all of a sudden 
Outlook on the Web jumps to the foreground. This has happened enough times that 
I don’t believe it is just chance or some accidental hotkey combination. 
Another complaint is that it does this in the middle of them typing an email. 
I’ve asked them to keep track of how often it happens, and I can find no 
pattern.

The users are running Windows 8.1 ent v6.3 build 9600 and patching is kept 
current via BigFix.

This seems to happen no matter which browser they are using – IE, Chrome, 
FireFox…..they all seem to do it.

Any ideas on what the cause might be and what can be done to resolve this?

Thanks,

Jonathan
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