Depending on your current OS version have you tried the Update Manager?  System 
Menu -> Administration -> Update Manager.  Wait for it to search your 
repositories and find any updates.  Click "Update All".  On the window that'll 
pop up click "Details".  You might find some useful information and errors 
there.

An alternative would be to update via the command line as this tends to report 
more useful errors.  If you wanted to go to build 105 from the /dev repository 
try this:

# pfexec pkg set-authority -O  http://pkg.opensolaris.org/dev 
opensolaris.org-Dev
# pfexec pkg set-authority -P opensolaris.org-Dev
# pfexec pkg authority
AUTHORITY                           URL
Blastwave                           http://blastwave.network.com:10000/
opensolaris.org-Contrib             http://pkg.opensolaris.org/contrib/
opensolaris.org-Dev (preferred)     http://pkg.opensolaris.org/dev/
opensolaris.org                     http://pkg.opensolaris.org:80/
extra                               https://pkg.sun.com/opensolaris/extra/

# pfexec pkg refresh
# pfexec pkg image-update


If you need more help it would be useful to provide the following:

Q: What OS are you currently running (uname -a)
Q: What repositories do you have configured? (pfexec pkg authority)
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