Regular Expressions 101

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"
\d{1,2}\/optimized\/.+\.tif
"
g
\d
matches a digit (equivalent to [0-9])
{1,2} matches the previous token between 1 and 2 times, as many times as possible, giving back as needed (greedy)
\/ matches the character / with index 4710 (2F16 or 578) literally (case sensitive)
optimized
matches the characters optimized literally (case sensitive)
\/ matches the character / with index 4710 (2F16 or 578) literally (case sensitive)
.
matches any character (except for line terminators)
+ matches the previous token between one 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)
tif
matches the characters tif literally (case sensitive)
Global pattern flags
g modifier: global. All matches (don't return after first match)
Your regular expression does not match the subject string.

Regular Expression
No Match

r"
"
g

Test String