Reducing size of PDF not working

Does anyone know why when trying to reduce a PDF by selecting Save As then choosing Reduced Size PDF wouldn't work on certain documents.  I did several PDFs and it worked fine.
I have a bunch more that are over 1 MB and are too big to be emailing so I need to make them smaller.  Some appeared to work but the size didn't change others I get a box that pops up with a Conversion Warning... An error was encountered while saving the document.
Thanks

Try File menu >Save As... > Otimized PDF
When Optimizer open click Fonts Tab.
See how many copies of each font style (Bold. Italic, Bold Itallic, etc) yu have.
Remove all copies except one (example if you have 5-6 copies of Helvetica Italic which is frequently Possible) remove all copies except one.
I seen cases in PDF I have created where had as many as 6-7 copies of the same font version in the same PDF and maybe multiple font versions  often reducing the size by as much as 75%. (Not usually But havehad  it happen.)
Also click on the Tab for pictures unless you plan on printing a business report, 200dpi/ppi is the most you should use.
Save as a slightly different version. Open new version and check the size.

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