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Some observations and questions:
1. When you "print to PDF" you're using ArcMap's printing functionality to a "virtual printer" - in this case provided by Adobe Acrobat. You will need to contact Adobe's technical support for issues you are having with this functionality as it is wholly their product.
2. ArcMap has built-in Export to PDF functionality which may meet your needs. Is there a specific reason you are not using it?
Jeremy, thank you for your prompt response!
1) I have yet to bring this up with Adobe customer support. I have come to realize that the setting can permanently be changed for all future [new mxds] but any existing mxd that I have created back when I was using 9.3.1 has automatically checked on "Rely on system fonts only" - [this is what results in the error prompt]. It is only when I check off the setting and save the mxd, the Print to PDF function works. But this is something I can resolve with what you recommend: to bypass this completely by using "Export to PDF".
2) Yes, originally in the past the reason I have resorted to "Print to PDF" as opposed to "Export to PDF" dealt with the issue of point symbols [in my case its usually well symbols] using ESRI Fonts. Even though I have the option selected to "Embed All Document Fonts", I would have non-ESRI workstations displaying strange character types [which my understanding is do to the ESRI font library missing from that workstation]. This was a past fluke and I just tested "Export to PDF" with the "Embed All Document Fonts" checked on and this does not seem to be the case anymore.
I would hope there is some work around to avoid seeing this error so frequently if I use the option to print to a virtual printer, but in the meantime I will use the export to PDF option. Thank you!