There are three areas you need to look in.
vBulletin Options > vBulletin Options > Message Attachment Options
Go through all of this and make sure all of the settings are to your liking. Make sure the allowed per post is greater than one.
Attachement > Attachment Manager
Ensure that all of the types you want are enabled.
Forums & Moderators > Forum Permissions > Edit
Be sure that Can Upload Attachments is set to yes for each usergroup.
These are the three ontop of already having them set in the usergroups, themselves. If those still don't help you, talk to vBulletin.com to see if there's something wrong with your installation or to get technical support.
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