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Preview will not 'flip horizontally'  a pdf

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Recently I just upgraded to 10.4.10 (from 10.3)...Using Preview to open a PDF, it will no longer flip (mirror) a pdf file vertical or horizontal. The option to do so shows in 'tools' but the text is grey like the command is not available. It will however, flip a jpeg or tiff. If there is not a fix for this, then what about installing an older version of Preview on the newer OS? How would that be done?

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What did you convert to PDF? And how did you convert it?

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