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# Perl, 113 bytes

reads line from stdin formatted as the test cases. Exits with 1 valid or 0 if invalid.

```sh
perl -lF,. -E'($_,$n)=@F;@r=map{$n=~s/.{$_}\K/.*/r}1..length$n-1;$"="|";exit(!/$n/&&((y/ //d,/.$n./)||/^(@r)$/))'
```

```sh
perl -lF,. -E'
    # load clue and word
    ($_,$n) = @F;

    # create all permutations of prefix + ".*" + suffix of word
    @r = map {
        $n =~ s/.{$_}\K/.*/r
    } 1..length$n-1;

    # set array->string interpolation character for use in regex
    $"="|";

    exit(
        !/$n/ && (               # word not in clue, and (
            (y/ //d,/.$n./) ||   # is word break, or
            /^(@r)$/             # is bookend )
        )
    )
'
```



[Try it online!][TIO-mnt9shfw]

[TIO-mnt9shfw]: https://tio.run/##ZU5NT4NAEL3vrxibtYBu2fbgiWCKLbWkwJLdJU3jB9GI2qRuCdCkpq0/XVzw4MHLzLw3896bIi83V82uyqHaPVdg5Pt1bThIA2hHE1twgKJcqxpwdjd8uBzCCXX4FYzzCgbXYBCcOY2JM4KV5Y5nzrh0P56KA1buV0XtA85O9wtqX9DyNLLtTa7e6nesBiMH99zesed0OWcUK9rvm@YnBUpfCLWxsql1PNJHc1xamFpW0ySMcZizVPgE@JwhEcS3oQ@Se5MFARFMFmjFUohSIWHKJGjAIRDgxVOYcCbELyMFgVXKpUBCdqvQ97jWS48jySDS7pJFPgpi8CDRrqFmYi9BQZRwlvgcug/0oPu/J1okURJ6sSa12JcENNG6S@23/ItaMrgJ@FTAMpBzYPpeSF3b9NhH39uiXm9V1Qw2M2L/AA "Perl 5 – Try It Online"