Dialplan Confusion (Outbound Routes)

Apparently I am not understanding outbound routes well. I recently ordered a new SIP trunk that will be replacing my legacy PRI circuit. I wanted to test outbound calling while leaving the PRI for everyone else to use until I am satisfied with the results so I added another outbound route that duplicates my primary route but added a prefix of 8 to every entry, but that does not appear to work. When I use an 8 in my dial out, the outbound call still uses the PRI trunk (including the 8 I have added). The call log shows the complete number that I dialed (including the 8).
My dail plan has the following match numbers:
011.
1800NXXXXXX
1833NXXXXXX
1844NXXXXXX
1855NXXXXXX
1866NXXXXXX
1877NXXXXXX
1888NXXXXXX
211
311
411
511
611
711
911
933
NXXNXXXXXX
NXXXXXX

As I said, the second outbound route has the same entries with an 8 added to prefix.

This is more acedemic than anything else, but I would really like to understand why this is not working.

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I missed one entry in the match, I also have:
1NXXNXXXXXX

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