Do you get the TortoiseSVN context menu at all when you right click? If not, can you try holding down the shift key when right clicking (that should bring up the old context menu)?
TortoiseSVN adopts the context menu so if you right click in a folder that is NOT a working copy, you will not get the Cleanup (Update, Commit etc.). Are you sure the folder you are in is also a working copy?
There is a known bug in 1.14.2 and earlier if you use tabs in Explorer, where the folder is taken from the first tab and not from the current tab. This has been fixed in the development version.
Kind regards,
Daniel