I came across this problem recently on a new Windows 2008 / IIS 7 server using classic ASP.
We have a client website that uses sessions for authentication but if you authenticated and then switched from http to https or vice versa the session seemed to drop.
After a while searching the ‘net and a bit of head scratching I found the answer.
Under IIS manager, click on your server name in the left panel and then double click on the ASP link from the middle panel. Open the “Session Properties” section and set “New ID on Secure Connection” to FALSE. Click apply in the top right panel and you’re good to go.
No more dropped sessions switching between http and https!
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