This question has been answered by BobRay. See the first response.
ALTER TABLE modx_site_content MODIFY description VARCHAR(some bigger number)
255 is not the number of characters you can store. It's the number of bytes allocated for that field (minus a null byte and sometimes bytes for indexing).
Is your character set utf8mb4? That would explain it.
If so, changing to utf8 would fix it, but so would just changing the field in the DB to a larger VARCHAR. It doesn't hurt to go up in size, though going down can truncate your data.
On the SSQL tab after selecting the DB in PhpMyAdmin:
ALTER TABLE modx_site_content MODIFY description VARCHAR(some bigger number)