re = /Debug.*?endmsg(*SKIP)(*F)|restart-required/
str = 'Debug: testing message with no restart-required.endmsg.Warn:garbagestuff.Debug: another message.endmsg.Warn:moregarbage.Debug: this testing message has restart-required.endmsg.Error:server 404 not found.Critical restart-required. Debug: blah blah restart-required.endmsg.'
subst = ''
result = str.sub(re, subst)
# Print the result of the substitution
puts result
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Ruby, please visit: http://ruby-doc.org/core-2.2.0/Regexp.html