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Who can I send my diagnostic log to?
Pressing ALT OPTION on cloud icon doesn't show anything.
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The best place to request features and report bugs is on the following forum, which is monitored by the engineering team:
https://feedback.photoshop.com/photoshop_family/categories/photoshop_family_lightroom_cc
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Also have you tried to filter by syncing, this may show the problem file.
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Yes I have tried this. No files show up when filtering for Syncing files.