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Hey glennsharrock - just a couple of questions as this is very curious...
When you run Data Masker against the instance, is Masker installed on that same server as the instance it's pointed against? Are you using the same install of DM when invoking independently and against the image?
Are you running any other preparations against the Image whilst creating it? Any custom SQL Scripts or anything?
If you've got logs handy for both runs (and want to just remove the top bits with server names) then I (and probably the RG folks too) would be jolly interested to see them
DM Logs outside Clone > The Misc. Setup Tab - Data Masker - Product Documentation (red-gate.com) "Directory for Log Files"
DM Logs inside Clone > SQL Clone Dashboard > Activity > Find the Image Creation Activity > Logs
KR -
I think issue is ok. getting different results when running
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(SQL Clone v5.3.27.4396)