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Appears to be a known bug with CkEditor, 8.5.2 & XPages Persistance settings
"We have an existing issue with images submitted via the ckEditor in 852 that we're seeking to address as soon as possible and get a fix into the first fix pack for 852. So if you're hitting this it's recommended that you log a support call for it and reference this bug number (SPR#) PHAN88HEKA. With your help we can get this addressed quicker.
There is a workaround, though this will not be to everyone's liking as it effects performance.
Go to the Application Properties and on the XPages tab set the 'Server page persistence' to either "Keep pages in memory" or "Keep only the current page in memory". You will need to apply this on an app to app basis"
Feedback response number WEBB8A9AUS created by ~Holly Opkilyader on 10/15/2010