I don't shop Amazon much and have discovered the problem you describe.  Have started just recording each purchase separately, instead of the "bunch" that I order.  If you do much shopping on Amazon I don't know how that would work, would imagine that would be too much work.

I personally would budget the whole amount and then post the transactions as they happen not as one chunk.

are you a Prime member?  if you become a Prime member (shipping is free) then you could limit your shipping entry to the $90 a year, and put in as your long term budget. 

I do a split at the time of purchase (and add a note against each split item to state product the cost relates to): 

Then if they do come in bit by bit across my bank account I add the line item as a new item in my account (again with a note to say what the product was) and mark that as cleared:

...and then edit the original split transaction and delete the individual line item which came in separately (note the minus symbol beside each split item).  At the time of doing this I need to edit the total amount of that original outflow amount in order to allow that to save correctly:  

This then allows me to clear the remaining items if they come in to my bank as one transaction, else repeat until all are split out into individual transactions and cleared. 

I'll put in the original amount and then fix it.  It is actually usually easy to fix if you know the trick... After a short time after the order got to amazon and go to your order history and then click the 'view invoice' link that his hidden to the top right of the order it breaks down the order per charge on the card correctly 99% of the time.  

Where this process doesn't work for me is during Christmas and my Birthday when my wife orders me presents and I'm not allowed to look at the orders/invoices.

Add every item as an individual transaction in YNAB as soon as you order. Then clear the transactions in YNAB as they clear in your checking account. Done :)

Also, if you use the Amazon Visa (Chase) credit card, it will have the Order # with the transaction amount. But unfortunately, it is still a manual process of looking up the Order # on Amazon to correctly categorize the orders.

I include the order number(s) in the memo section so I can tie them back to my original entry.  

Man, it's Christmastime and I'm in the same boat James is in right now. Super stressed my wife out cause she couldn't find the numbers in her Amazon orders that showed up on our card in YNAB. Not fun.

I make a paper list from the Amazon order in columns, each column represents a category. Then I add them up on a calculator. Then I get the bank statement and add them up. If the two lists don't tally I make a guess at which category the missing few pounds (it isn't much) goes into.

It is a tedious PITA, but I can't think of a better way. 

To be honest, although boring, it doesn't really take very long. Maybe 10 minutes. <shrug>

Something I saw on Reddit: Don't bundle items. If you order things as you need them, instead of making big purchases all at once, this situation will fix itself. 

But, like others have said, this the easiest thing (for those on Direct Import):

1) Manually enter in the ENTIRE transaction

2) Split accordingly in YNAB

3) If/when Amazon divides the transaction into smaller orders and they post to your Amazon Visa card (the ONLY car you should be using on Amazon [5% cash back!]) delete your manual entry. Boom. 

I haven’t encounterd this yet but it sounds like the ability to match multiple downloaded transactions to a single manually entered transaction would be handy. 

Adding the order number to the memo field has been kind of a game changer for me to figure out what was what when I have to go back and split it up into multiple transactions. It's challenging to find the actual transaction total otherwise.

I've really been struggling with this lately. I buy so many of my essential needs from Amazon that it gets very confusing.

I've tried  2 methods: only ordering 1 thing at a time. Put it in my shopping cart, go to check out and buy it. Do the same with the next item. Then you get all separate transactions and know exactly what it's for when the transaction clears. My hesitation in continuing this is that it's wasteful and I don't want to receive 6 separate boxes at one time.

The only other method I've used that sort of works is to enter the entire amount of the transaction as soon as I order it. Then as each transaction imports, I clear each one of those until the total adds up to what the original amount was. Then I delete the initial transaction that I manually entered when I completed the order. This too though is a PITA.

Neither is perfect and if someone has discovered something better, please pass it along!

I spent a frustrating amount of my evening last night trying to reconcile my Amazon purchases instead of working on my sewing project. I managed to figure it out, but I definitely! want to streamline that process if I can. Based on what I learned in this thread, I'm going to record the transaction, split it according to the orders (putting the order# in the memo) as listed in the order confirmation email and hope it all matches the next time I reconcile.

My struggle last night was down to Amazon originally giving me one order with 3 items totaling one number, later splitting it because one of the items shipped later, thus changing the original split and having unrecognizable entries in YNAB. Ugh. I think I had YNAB, Amazon, 3 calculator windows and both the credit card statement and the running register open at once trying to get everything to work.

I enter the initial transaction (assuming all the same category), and then as each shipment clears the bank, i will approve each transaction and go reduce the original transaction I entered by that amount.  This way, the ledger is always accurate.  The problem with leaving the original transaction unedited is that now your budget is incorrect.  Just as an illustration:

I spend $100 at Amazon and put in a transaction for $100.

They split that into 3 shipments, one for $25, one for $60, and one for $15.  Let's say they each clear the bank on different days (so the maximum annoyance 😃).

On day 1, I approve the $25 transaction and reduce my original transaction of $100 by the same amount (so it's now $75).  Then $60 get's approved on day two and I reduce the original transaction again (so it's now $15).  Then, when the last shipment clears the bank, the amounts match (both $15), so the transactions link and I approve.

This method makes sure that your budget is always accurate, that you know how much is left to clear from that order, and you get the last transaction to link for free since the amounts will match.

Hope this helps!

Another tip is the individual sellers will be separate orders, guaranteed. You might as well record them separate from the get go.

However, "fulfilled by Amazon" counts as Amazon, and is likely (but not guaranteed) to be lumped into a single transaction.