Lightroom 5.4, syncing photo settings edited in CS6 does not work. Maverick OS 10.9, Raw 8.3.0141

I recently updated Lightroom to 5.4 and noticed that when the file comes back from CS6, the edit/sycn settings does not work. Selecting the gray area of the source file, and selecting another, clicking on the sync produces nothing. When I select a source image and another that has not visited CS 6 the sync works fine. I have used this simple technique for years with previous versions and never had a problem. Something has changed with the update and/or compatibility with the file coming back into Lighroom. Any thoughts about this would be appreciated.

ssprengel, thanks for following up. I work with DNG files in Lightroom that have been converted from Raw CR2 files. They are exported from Lightroom to Photoshop as Tiff files and any files that i edited and traveled round trip could not be used to sync other files in Lightroom. Even simple edits like saturation or exposure have disabled the file from being able to sync the settings to other files. I do most of the syncing of develop settings in Lightroom, but occasionallly I will adjust basic settings in Photoshop for one reason or another and after updating to 5.4 I noticed that sync worked fine within Lightroom only. I have tried a few changes to preferences with regard to how develop settings are registered with the file and that hasn't made any difference. Any ideas?

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