Issues may occur when exporting custom symbols or fonts to a PDF file in ArcMap. Instructions provided discuss how to work around or avoid unwanted results.
For any major text errors, refer to the Microsoft Font Validator:
Microsoft Font Validator
The Font Validator tool evaluates font files for their adherence and generates errors when a problem is found that may hinder the font from exporting. Major errors include intersecting contours, duplicated contours, and misoriented contours.
Issues may not be found with a font validator. However, the most common errors encountered with text validation are considered with this tool.
If the font was created by the user, Microsoft provides guidelines for creating TrueType and OpenType fonts and includes standardization text for successfully exporting in PDF documents:
Developing Fonts: Overview
For character marker symbols to work correctly with a font using Latin characters, the ISO-8859-1 character set requires that the font must cover characters 33 – 255 (with exclusion of characters 126 – 160). Fonts are limited to 188 characters per TrueType Font Family (ttf).
If glyphs have been renamed internally, the change can cause major problems in a Latin Text font. This affects how the characters are mapped to the keyboard. If renamed, the glyphs return a value of “Not Defined”.
It is not permissible to cross (intersect) contours. This is a large issue which is displayed in the screenshot below.