Cancelled Pending Credit Card Transactions
I have a pending credit card transaction that I know will be cancelled/dropped and not cleared.
If I accept it - and then once bank drops/removes the pending transaction (e.g cancelled order) - I would assume my balance would then be permanently out of sync since I've already imported the pending transaction.
When the bank removes the pending transaction - there isn't going to be a record for it for YNAB to merge it as an offset - so it feels like importing any pending transactions is dangerous in case the transaction is cancelled.
How should this situation be handled?
I don't recommend that you blindly accept all pending transactions. If you know it will never clear, then just don't accept it. However, a mistaken acceptance isn't the end of the world.
The pending transaction -- if accepted -- will not be cleared. Part of my reconciliation process is to look at any uncleared transactions remaining after reconciliation to evaluate whether they are legit. If something is not legit, then I get rid of it. Typically for me, they're either still pending on that card (so I leave it) or they are legit charges, but manually entered in the wrong account (so I move it).
This same issue has existed for a long time outside of the import scenario. Occasionally, a vendor screws up and doesn't actually charge my card. After a few months of my manually entered transaction sitting at the bottom of my uncleared transactions, I just delete it. For a mom & pop store, I've gone back to them at that point to try to pay, but they said, "our mistake, just keep it"; I just left it in the tip jar. After a couple repeats of this, I now just use cash at that store. That "dangling" uncleared transaction messes with my OCD. 😑
Like Annieland indicated, if you simply ignore a pending transaction, it won't appear as a Pending Transaction when it's no longer pending at your bank. This is the same if it's simply dropped from your bank because it never clears, or if it's imported as cleared.
In this case, it seems like ignoring it and letting it drop is the best solution! :)