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Make sure that you are specifying a path only (i.e., without \srcsafe.ini at the end) for your SSDIR_WEB macro. The SourceSafe action will strip that off if found, but SSHELPER doesn't.
I added the steps below in the SourceSafe.bld sample (right after the Open Database step) and they worked. I did notice a couple things:
1) you may also want to specify a username/password
2) those operations return an exitcode of 1 on success, so I changed the exit code range to include that.
<step action='Run Program' type='0'>
<command>%SSHELPER% "%SAMPLEDB%" Cloak $/Executables -y%SSUSER%,</command>
<indent type='3'>1</indent>
<name>Cloak</name>
<outputfrom type='3'>1</outputfrom>
<successcodes>0:1</successcodes>
</step>
<step action='Run Program' type='0'>
<command>%SSHELPER% "%SAMPLEDB%" Decloak $/Executables -y%SSUSER%,</command>
<indent type='3'>1</indent>
<name>Decloak</name>
<outputfrom type='3'>1</outputfrom>
<successcodes>0:1</successcodes>
</step>
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