From @ShimmerFairy

$ perl6 -e 'my token foo { foo { say $/.to } }; "foo" ~~ /<foo>/'
3
$ perl6 -e 'my token foo { {} foo { say $/.to } }; "foo" ~~ /<foo>/'
0

It seems that $/ is constructed only in the first code block of a regex, and not reconstructed for subsequent blocks. Compare to $¢, which reports the right position in any case​:

$ perl6 -e 'my token foo { foo { say $¢.pos } }; "foo" ~~ /<foo>/'
3
$ perl6 -e 'my token foo { {} foo { say $¢.pos } }; "foo" ~~ /<foo>/'
3

Note that trying to construct a Match from the Cursor doesn't work around the issue​:

$ perl6 -e 'my token foo { {} foo { say $¢.MATCH.to } }; "foo" ~~ /<foo>/'
0

From @smls

This bug is still present in​:

  Rakudo version 2016.09-21-g3ed51de built on MoarVM version 2016.09
  implementing Perl 6.c.

The RT System itself - Status changed from 'new' to 'open'

From @smls

This has been fixed by TimToday in April, in one of these commits​:

  https://gist.github.com/Whateverable/23122ebe34ebeccfdfc3cd04845c54f4
  https://gist.github.com/smls/aff6a56c1cfcce5c7779251aee394e42

Tests needed.

From @zoffixznet

Tests added​: Raku/roast@c8a7565a68

@zoffixznet - Status changed from 'open' to 'resolved'