Song plays don't upload - even though you already tried everything in cs188's post?

Leave this page open and next start the certificate manager.  Select Start, Run and type “certmgr.msc”

You’ll see a window similar to the one below:

http://cid-390f118edc5ea612.skydrive.live.com/self.aspx/Public/fiddler4.jpg

Find under Personal Certificates the “DO_NOT_TRUST_FiddlerRoot” cert and drag this to the Trusted Root -> Certificates folder. 

You now have fiddler setup to monitor HTTP and HTTPs connections.

This indicates that HTTPS connection monitoring is working.  If you double click on one of the entries above with the HTTPS you can then inspect the contents of the web exchange.

Saving Fiddler Traces

1.       Start fiddler

a.       If you already have fiddler running, you can clear the current fiddler trace with control-X

2.       Start Zune and repeat the test of logging in, playing a song, and closing zune

3.       Go back to fiddler and find the line where the url is usage/upload

4.       Right click on that line and select File, Save, Sessions, in Archive/Zip

5.       Specify a location / filename (e.g. Desktop, Fiddler Trace)

6.       If it prompts you save all sessions select No

What To Look For

-- Do you have a line that says under "host" stats.zune.net, and next to it under "URL" usage/upload?

If it's in red and has "500" in the "result" column, you may have a bad character in your metadata. You should click on that line on the left, then click on "Session Inspector" and "Raw" on the right. You should see a list of the content Zune tried to upload; look through the list of items that look like this:

CountryCode=US&Locale=en-US&Usage=PlayStream,ZunePCClient,BF72CE00-0100-11DB-89CA-0019B92A3933,,2008/07/02:18:43:44,1

And try to find one that has a non-alphanumeric character in it - perhaps a box to replace a real character or something. The item in your library that corresponds to that line item may have something in it that causes your play uploads to get stuck. Fix the metadata, then try to upload plays again (by closing and re-opening the Zune software, signing in and checking the Web site).

If You Don't Have A Line That Says "usage/upload"...

If you don't have that line, your Zune software isn't even trying to upload your plays.

Try this, though it's not a full solution.

Find the hidden file “zunestore.sdf” – you’ll have to show hidden files and folders.

If you’re on Vista, it’s at C:\Users\<your username>\appdata\local\microsoft\Zune -> replace <your username> with whatever you log in with.

If you’re on XP, it’s C:\Documents and Settings\<your username>\Local Settings\Application Data\Microsoft\Zune.

Rename this file to zunestore.sdf.old. Then follow the directions for Fiddler again and see if you can upload a song you play. When you first open the Zune software after renaming the file, you’ll have to let your library rebuild.

If this works to upload your plays, there may be an issue with your Zune database. You can go forward like this, but you'll lose any of your play data stored in your old database. You also might find that some customizations you did to your music library are gone (because they were stored in the old database).

You can help Zune staff learn more about what's going on in your database by going to skydrive.live.com and uploading your old Zunestore.sdf. Send me a PM with the URL of your database and we'll check it out.