Okay, so if I keep putting in my id and password then I get a small windows box with the following wording:

"Access to the resource was denied. If you have signed into and saved your Microsoft account with a web site, sign out of that web site, and then try this operation again."

Had the same problem, too. I think I've fixed it by removing the TripIt calendar from my list of Outlook's "Other Calendars". I didn't find it useful, anyway; YMMV.

Same here... I always thought it had to do with using a proxy within Outlook (to avoid the need for VPN), but maybe not? I also deleted it from my Outlook calendar, but I would like to have it back. Any chance it's related to the notice to update the iCal feed a few weeks back? I'm thinking it's possible I updated the iCal feed in Google but not in Outlook...

You got a notice from TripIt about updating the iCal feed?

This.

There was an email that went out. I don't remember the specifics of it, but it said something about refreshing your link to avoid interruptions.

I sent a note to TripIt Support and they suggested either refreshing or completely redoing the iCal feed. I chose to delete and start over and for now there are no issues.

TripIt said the complication I experienced was linked to their "enhancement of the security of the iCal feed".

About 1 month ago, I got an announcement that TripIt was changing its feeds and that users should go in and get the new feed address/link and update their respective calendar programs (I use both iCal on a couple of Macs, Calendar on three iPhones and two iPads and Outlook (2013?) on a Dell Inspiron PC Running Windows). Update all the feeds back then and I have not received the error messages (touch wood).

Right. The new feed starts with https. That's the new security enhancement they mention in the e-mail.

Seems like this was the issue and it was resolved by updating the iCal link. I had done so in Google Calendars when the original notice was sent out but didn't even think about doing the same in Outlook (both 2010 and 2013 on multiple machines, same issue).

I also got the same message- for days- so I just deleted tripit from my outlook- then went to their web site- went by their instructions to reinstall- - worked- no message anymore- if it had not - then that would have been the last of tripit for me.

Moving to Travel Tools...

Damn it - I had all of the same problems as above! So I deleted TripIt from my Outlook, and now I just can't add it back... Outlook 2010 doesn't seem to recognise the new file as a Calendar feed (although Gmail calendar does!)

I've tried all manner of little tricks, but nothing. I just can't get it to work. I get getting parsing errors too, and my IT guys are stumped too.

Anyone else manage to fix all this? I emailed TripIt support, and they politely pointed me to the help pages, showing how to add the feed to your Calendar, and completely ignoring my explanation that I had already done that, and what the errors were.

I rely heavily on my TripIt feed in Outlook. Really need to get it back. :(

Also - sorry, last point, when I go to their website, and look for my iCal feed - it appears as: " https://www.tripit.com/home# "

Which is clearly wrong. I mentioned that in my email to Support too, but they ignored that part.

Anyone else seeing the above? Or still having issues?

This is the Send/Receive error I get for my TripIt feed:

Anyone else get that? Any ideas how to fix it?

Did you add it this way: Click on Folder; then Open Calendar; then From Internet; then copy in the URL from your TripIt account (it should start with https: )
This worked fine for me with Outlook 2010.