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I often import or place files in to my Omnigraffle files - mostly EPS or PNG format. I often do this by drag-and-dropping from the finder in to OG.

Often it doesn't work and I have to restart Omnigraffle and reopen the .graffle file. Once this is done the 'place file' works first time every time.

I have had this issue for years on different Mac OS and OG versions. Can anyone help?