Sperry Software uses several 3rd party components (known as DLLs) in it's solutions.
Occasionally, these products fail to install properly for various reasons (frequently (but not always) because they are shared across other competitors products, and the versions do not match up).
You'll know that this may be the problem if you enable writing to the log file, and look in it and search for the words "Error occurred". Look to see if there are errors like:
Reason: Unable to cast COM object of type 'System.__ComObject' to interface type 'Redemption.SafeRecipient'. This operation failed because the QueryInterface call on the COM component for the interface with IID '{5C61669E-F0CE-4126-B365-316588E6228F}' failed due to the following error: No such interface supported (Exception from HRESULT: 0x80004002 (E_NOINTERFACE)).or
Error occurred at line 125. Reason: Unable to cast COM object of type 'System.__ComObject' to interface type 'Redemption.IRDOMail'. This operation failed because the QueryInterface call on the COM component for the interface with IID '{D85047E0-7767-4D48-86B6-28BDB5728ABB}' failed due to the following error: No such interface supported (Exception from HRESULT: 0x80004002 (E_NOINTERFACE)).There are several other versions of this error. They all mention the word "Redemption".
To fix these problems, follow these instructions:
Exit Outlook
Go to Start and type "cmd" to begin a command line prompt
In it, type these instructions:
C:\Users\{your username here}> cd \
C:\> cd "Program Files"
C:\Program Files> cd "Common Files"
C:\ProgramFiles\Common Files> cd "Sperry Software"
C:\Program Files\Common Files\Sperry Software>regsvr32 /u SSOutlook64.dll
(click ok to the prompt)
C:\Program Files\Common Files\Sperry Software>regsvr32 SSOutlook64.dll
Restart Outlook
Try to reproduce the problem again
Note 1: It may be the case that you cannot "cd 'Sperry Software'" because it doesn't exist. In that case, try going to "Program Files (x86)" in the prior step(s) instead.
Note 2: It may the case that SSOutlook64.dll cannot be found. In that case, substitute "SSOutlook.dll" for "SSOutlook64.dll" in the two steps above.