Request clarification before answering.
Hi Scott,
do you try to debug the preview or the creation of a new output?
If you want to debug the creation of a new output, check in transaction NACE the relevant condition records.
As "Dispatch Time" (or "Transmission Time") 4 should be costomised for your debugging.
Example:

Compare https://help.sap.com/saphelp_erp60_sp/helpdata/en/a0/86ce53118d4308e10000000a174cb4/frameset.htm
Regards,
Hubert
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