Outlook.com: Your session has expired please login again

The only workaround to this that seems to work for me is to NEVER type in the email address for the recipient until I am ready to actually send it.

So, that hints to me that the problem lies somewhere within the Outlook Contacts realm. 

Since I started this technique I have not lost any drafts.

Thanks for the tip.  I shall try not adding the recipient address until I have finished the email.

That brings me on to another gripe with Outlook Contacts (or 'People' as it is called) insists on putting the post code before the county which in UK is wrong.  It means if I copy and paste the address into my label software I have to rearrange it.

Same problem here. Been going on now, on and off, for about 3 months. I'm using Waterfox so, does NOT appear browser specific or update related.

Sometimes after the first 'time out' it can repeat this annoying episode 2 or 3 times in the space of 3 - 5 min meaning I have to try retyping the same email several times before the next *CRASH*.

I appreciate that Outlook.com is a 'freebe' but why include it in the package if it don't work properly and cannot be trusted?

I am still waiting for Microsoft to address the issue of how to attach one email to another. They have come up with one answer after the other, non of which addresses the central issue of why I can't simply attached a previous email to the one I am now sending.

Perhaps it is now time to try another email prog............

Hi Syed,

Is this problem ever going to be resolved?  This has been ongoing for many months now and affecting me in both Internet Explorer and Chrome browsers - and based on other answers in this thread, a lot of users are being affected in a whole variety of browsers.

It always happens when in the middle of typing in an email, and is extremely annoying, and often happens 2-3 times in a row before allowing the email to be completed & sent.

And despite the message saying the session expired and to sign back in - re-opening outlook will auto login so that no actual login is required.

Can this please be sorted so that outlook will function normal as it should - and "session expiry" does NOT happen whilst actively using outlook.

Thank you.

Looking forward to a response from Microsoft.

Same crap here.  Was doing it alot in the past, but stopped, now doing it again. Seems to happen with I reply to someone. I only wish Gmail had a better interface, I'd switch in a heartbeat.

I just lost an hours work when I deleted 1 live link in the email I had spent an hour writing.  The whole body of the email was deleted instead of just that link.  It is annoying as Hell.  I'm on Windows 7.1 X64 using Firefox 54.0

I constantly get logged out when I am reading emails, get told my session has expired after just 5 minutes of writing an email and often lose what I have written when I do log out.  This has been going on for months and is making it almost impossible to send emails. 

If it wasn't for Yahoo's abysmal security I'd move all my email over to Yahoo and forget the mess that hotmail has become on outlook.live.com.

Just over 1 month to go now before this problem/fault reaches its (first) 1 year anniversary since it was first highlighted.

'Normally' anniversaries are remembered for the  pleasures they represent. I wonder if the Microsoft team responsible for this little 'cock-up' will be celebrating and what the toast will be?

Or perhaps they are waiting to notch up the "second successful year" before breaking out the bubbly?

Cheers Microsoft, happy anniversary :(

this is the same what happend to me almost daily, it does not matter if it is a Laptop or the Desktop, I know w one constant ist Come. 

Also like to add that when this happens that it will not safe the draft to the point where it stooped and it also will not mail anything.. found out from a international letter that had to be mailed  and did't make it, what was in the Draft was a 1/3 of the Letter composed.