I have recently had the same trouble and just emailed the Groundspeak people about it. I picked up a TB on Oct. 11th and logged it as such. My log appears on the TB's page. Then all of a sudden, another log appeared saying that I had left him at the same location! Not so. I have him still and was about to leave him in another cache. Because the system does not acknowledge that I have him, I can't choose to drop him off when I log my next cache.
~Phoebe, the puking cat!~