Replace non-word characters, unless given sequence matches - ruby

Question

I have a string like this:
"Jim-Bob's email ###hl###address###endhl### is: jb#example.com"
I want to replace all non-word characters (symbols and whitespace), except the ### delimiters.
I'm currently using:
str.gsub(/[^\w#]+/, 'X')
which yields:
"JimXBobXsXemailX###hl###address###endhl###XisXjb#exampleXcom"
In practice, this is good enough, but it offends me for two reasons:
The # in the email address is not replaced.
The use of [^\w] instead of \W feels sloppy.
How do I replace all non-word characters, unless those characters make up the ###hl### or ###endhl### delimiter strings?

Answer 1

str.gsub(/(###.*?###|\w+)|./) { $1 || "X" }
# => "JimXBobXsXemailX###hl###address###endhl###XisXXjbXexampleXcom"
This approach uses the fact that alternations work like case structure: the first matching one consumes the corresponding string, then no further matching is done on it. Thus, ###.*?### will consume a marker (like ###hl###; nothing else will be matched inside it. We also match any sequence of word characters. If any of those are captured, we can just return them as-is ($1). If not, then we match any other character (i.e. not inside a marker, and not a word character) and replace it with "X".

Answer 2

Regarding your second point, I think you are asking too much; there is no simple way to avoid that.
Regarding the first point, a simple way is to temporarily replace "###" with a character that you will never use (let's say you are using a system without "\r", so that that character is not used; we can use that as a temporal replacement).
"Jim-Bob's email ###hl###address###endhl### is: jb#example.com"
.gsub("###", "\r").gsub(/[^\w\r]/, "X").gsub("\r", "###")
# => "JimXBobXsXemailX###hl###address###endhl###XisXXjbXexampleXcom"