Regular Expressions 101

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"
^http[s]?:\/\/\w+(\.\w+)*(:[0-9]+)?\/?(\/[.\S]*)*$
"
gm
^ asserts position at start of a line
http
matches the characters http literally (case sensitive)
Match a single character present in the list below
[s]
? matches the previous token between zero and one times, as many times as possible, giving back as needed (greedy)
s matches the character s with index 11510 (7316 or 1638) literally (case sensitive)
: matches the character : with index 5810 (3A16 or 728) literally (case sensitive)
\/ matches the character / with index 4710 (2F16 or 578) literally (case sensitive)
\/ matches the character / with index 4710 (2F16 or 578) literally (case sensitive)
\w
matches any word character (equivalent to [a-zA-Z0-9_])
+ matches the previous token between one and unlimited times, as many times as possible, giving back as needed (greedy)
1st Capturing Group
(\.\w+)*
* matches the previous token between zero and unlimited times, as many times as possible, giving back as needed (greedy)
A repeated capturing group will only capture the last iteration. Put a capturing group around the repeated group to capture all iterations or use a non-capturing group instead if you're not interested in the data
\. matches the character . with index 4610 (2E16 or 568) literally (case sensitive)
\w
matches any word character (equivalent to [a-zA-Z0-9_])
+ matches the previous token between one and unlimited times, as many times as possible, giving back as needed (greedy)
2nd Capturing Group
(:[0-9]+)?
? matches the previous token between zero and one times, as many times as possible, giving back as needed (greedy)
: matches the character : with index 5810 (3A16 or 728) literally (case sensitive)
Match a single character present in the list below
[0-9]
+ matches the previous token between one and unlimited times, as many times as possible, giving back as needed (greedy)
0-9 matches a single character in the range between 0 (index 48) and 9 (index 57) (case sensitive)
\/
matches the character / with index 4710 (2F16 or 578) literally (case sensitive)
? matches the previous token between zero and one times, as many times as possible, giving back as needed (greedy)
3rd Capturing Group
(\/[.\S]*)*
* matches the previous token between zero and unlimited times, as many times as possible, giving back as needed (greedy)
A repeated capturing group will only capture the last iteration. Put a capturing group around the repeated group to capture all iterations or use a non-capturing group instead if you're not interested in the data
\/ matches the character / with index 4710 (2F16 or 578) literally (case sensitive)
Match a single character present in the list below
[.\S]
* matches the previous token between zero and unlimited times, as many times as possible, giving back as needed (greedy)
. matches the character . with index 4610 (2E16 or 568) literally (case sensitive)
\S matches any non-whitespace character (equivalent to [^\r\n\t\f\v ])
$ asserts position at the end of a line
Global pattern flags
g modifier: global. All matches (don't return after first match)
m modifier: multi line. Causes ^ and $ to match the begin/end of each line (not only begin/end of string)
Your regular expression does not match the subject string.

Regular Expression
No Match

r"
"
gm

Test String