re = /(?:^\K.*+\R?){6}/m
str = 'Question text
A. Answer Option
B. Answer Option
C. Answer Option
D. Answer Option
Explanation text
Question text
E. Answer Option
F. Answer Option
G. Answer Option
H. Answer Option
Explanation text
Question text
I. Answer Option
J. Answer Option
K. Answer Option
L. Answer Option
Explanation text
Question text
M. Answer Option'
subst = 'Explanation\\n$0'
result = str.gsub(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