How does the system know outstanding checks? If I enter them, what happens when they do come through the linked bank account. Are they entered twice?

You are correct that you should enter the Checks (Credit Card charges, etc.) when they happen. 

When you do a Bank Feed to sync your Accts with the Bank you will then go through a process to Match what the bank shows has cleared.  Most of the time the items will match automatically, but there is another section you'll see that are Partially Recognized and Unrecognized.  So you may also see items in there to manual match to what you have in your QBs Bank Register. 

Usually it works out okay, but every once in a while you'll find a transaction that doesn't match anything.  So you need to figure out if it is a error on you end (typo or forgot to enter it) or an error on the bank's side.  Then go from there for what action to take. 

And yes there will be times that a check you wrote 4 days ago is sitting there in the Register with the right date, right amount and QBs will still make you match it.  A pain yes, but better than if you manually had to match to the small print on the Bank Statement at the end of the month. 

As for Reconciling at the end of the month.  If you've kept up on doing the Bank Feed throughout the month, then there really shouldn't be any questions when it comes time to Reconcile.  You put in the date, closing balance, tell QBs to ignore future transactions and (hopefully) it all matches up and you're done in a few seconds.

Thank you! This is very helpful. have a follow-up question if I may. You indicate that transactions should be entered as they happen, however I thought this is what the bank feed is for. Basically eliminating the need for you to make manual entries. Wouldn't it be Ok to just enter the uncleared transactions that the bank feed has no knowledge of? 

Also, when you say "match", does that mean the two entries basically eliminate each other? 

Thanks again for helping a QB online novice.  

Thanks so much! This is very helpful. 

Matching means that after you do a Bank Feed in the first Recognized tab QBs will show you a Deposit for $200 you made on the 1st and it Matches with what the Bank has.  It might also see you wrote check #123 for $50 and #456 for $100 and the Bank has those too.  So they they end up in the Recognized section PENDING YOUR APPROVAL.  The reason you have to give the final okay is because the people that wrote the Bank Feed knows it can Match to the wrong item sometimes.  So you're the final say.  (I do it individually because I don't have that many items, but there is a Batch method too.)

There are also a Partially Recognized and Unrecognized Tabs that may have items.  Those are the ones that for whatever reason, QBs does not know what to do with them.  So you just need to click on the drop down (on the right) and Match them in the list of options.  This is where you'll see that everything is there and it should have Matched, but for whatever reason it didn't.  Or... you find something you forgot to add, so you just to add it.  And occasionally you might find something you have no idea what it is and you need to talk to the bank.

When you're done, all of these Transactions will show as "Cleared" in the Register.  Then at the end of the month when you go to Reconcile, you should only have Cleared items and you just accept them all and close the process.  If you haven't kept up on it, then you go through the process the old fashion way and confirm each item then.

And I see online a lot of people say they just use the Bank Feed for entries because they never knew what Bank Feed was created for.  It is to Confirm/Accept what Transactions the Bank has said they have made to your Acct.  It was never intended to just make entries and it's your cross check that there wasn't an error someplace.  And yes, it does allow you to just Accept and make an entry, because there you are going to find those things you forgot to enter.  But odds are the associated Acct (Expense, Liability, Income, etc.) may not be correct, so you'll have to check the entry anyway. 

Pending the business, letting Bank Feed do it for Credit Card Transactions may work.  But if you're entering Payments and doing Bank Deposits through QBs, the you will probably find errors.  Most Bookkeepers, etc. that I've worked with typically do it daily or every couple of days to keep thing up to date.  And then when the Bank Statement arrives, it should take only a few seconds to Reconcile.  Wait to catch the errors at the end and it's probably going to be more time than you want to spend on it.