This is one of the features that Ruby cribbed directly from Perl. The Ruby documentation seems really bad, in particular “interpolation mode” is grievously misleading.

Perl’s documentation is far more clear about the consequences:

(https://perldoc.perl.org/perlop#Regexp-Quote-Like-Operators)

   o   Compile pattern only once.

  […]

  PATTERN may contain variables, which will be
  interpolated every time the pattern search is
  evaluated, except for when the delimiter is a
  single quote. […] Perl will not recompile the
  pattern unless an interpolated variable that
  it contains changes. You can force Perl to skip
  the test and never recompile by adding a /o
  (which stands for "once") after the trailing
  delimiter. Once upon a time, Perl would recompile
  regular expressions unnecessarily, and this
  modifier was useful to tell it not to do so,
  in the interests of speed. But now, the only
  reasons to use /o are one of:

  [reasons]

  The bottom line is that using /o is almost
  never a good idea.

In the days before Perl automatically memoized the compilation of regexes with interpolation, even back in the 1990s, it said,

  However, mentioning /o constitutes a promise
  that you won't change the variables in the
  pattern. If you change them, Perl won't even
  notice.

Perl 4’s documentation is briefer. It says,

(https://github.com/Perl/perl5/blob/perl-4.0.00/perl.man#L272...)

  PATTERN may contain references to scalar
  variables, which will be interpolated
  (and the pattern recompiled) every time the
  pattern search is evaluated. […] If you want
  such a pattern to be compiled only once, add
  an “o” after the trailing delimiter. This
  avoids expensive run-time recompilations, and
  is useful when the value you are interpolating
  won't change over the life of the script.