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Enabling the OnLetterhead toolbar for Outlook 2010
2010 Toolbar

Click File > Options > Addins
At the "Manage" dropdown list at the bottom of the window, select Disabled Items
Click  "Go…"
Click OnLetterhead Outlook 2010 and click Enable
Click Close
Close and re-open Outlook


If OnLetterhead is found in the Inactive Items:


Click Go next to COM Add-Ins:

COM Add ins

Click the checkbox next to OnLetterhead Outlook 2010 Plugin:

Check OLH

Click OK

Usually this will immediately enable the OnLetterhead toolbar. If not, please restart Outlook and repeat these steps if necessary.