Avoiding creating debt...
Ok, so this is probably obvious but I just want to be sure. I got a little behind in dealing with YNAB. Now that I'm finally budgeting, I have these categories from September that are "overspent". Do these subtract from the next month, or do I need to fix them in order to avoid creating debt as the notice says?
I'm feeling confused...
In this case, only part of it is taken out of next month's TBB ($39.93). The rest is already debt on the CC, and you would need to budget toward the appropriate CC Payment category in some future month to enable a larger payment.
It appears you are trying to use the "temporary debt" approach to reimbursements, but also have cash transactions. If you have other budgeted CC purchases, you can often reallocate funds from the CC Payment category to the Reimbursement category, converting those cash transactions to new debt as well. (Nothing is taken out of next month, because it's all CC debt.)
This simplifies the reimbursement handling considerably. (If the Reimbursement category turns green, move those funds to the CC Payment category.) You should also be categorizing the reimbursement inflow into that Reimbursement category, and not as TBB as erroneously suggested in the YNAB docs.