Charter font printing issues in italics and bold italics in Pages

Since I cannot reproduce this font issue in Catalina 10.15.3 and Pages v8.2.1, that leaves your Canon printer as the wildcard. This particular networked device is supported by Apple's Airprint technology which will drive it without Canon drivers.

On your Mac, I suggest you Reset the Printing System…, and when you select drivers in the re-add panel, choose AirPrint, instead of the specific Canon drivers previously used. Once the printer reappears in your Print panel, control-click on it to ensure it is the default printer. Then print content with the Charter font characters that were problematic prior to choosing AirPrint, and see if the issue is resolved.

I cannot reproduce this issue with Catalina 10.15.3 and Pages v8.2.1. All of the Charter italic and bold faces for these characters image properly for me. Tested on a 2014 MacBook Air.

You could press and hold the shift key (until the boot progress bar appears) while rebooting to force the machine into Safe Boot mode. Does the font issue persist in this mode? Reboot normally, and test again to see if it was a transient gremlin, or if it remains.

You are welcome.