AutoCat - Behaves differently with blanks vs Run-Rules-On-All

I noticed AutoCat behaves differently when running it standard (Blanks only) vs Run Rules on All.

I have 2 transactions.

CASH APP*LOCKSMIT 02/08 PURCHASE XXXXX91940 CA DEBIT CARD *5502
CASH APP*SYLVIA C 02/09 PMNT SENT XXXXX91940 CA DEBIT CARD *5502
Category Full Description Contains Full Description Contains Account Contains Institution Contains Amount Min Amount Max Amount Polarity Description
Advertisement Cash App Sylvia negative
Key Cash App negative

My Autocat is set up with the following.

When both of the transaction categories above are blank and I run AutoCat (Blanks only), the correct categories are applied to those transactions. Sylvia is Advertisement and Locksmith is Key.

When both of the transaction categories above are blank and I run AutoCat (Run Rules on All), both Sylvia and Locksmith transactions have the category of Key.

If I move the Autocat row with Cash App + Sylvia + negative polarity below Cash App + negative polarity, the results are reversed. AutoCat (Blanks only) will have Sylvia and Locksmith as Key. AutoCat (Run Rules on All) will have Sylvia as Advertisement and Locksmith as Key.

Why is this the case? This might seem minor but it doesn’t give me confidence to apply Run Rules on All on a larger scale with thousands of transactions. I’m hoping to have some understanding for this. Targeting “Sylvia” only wouldn’t work as some other transactions are not advertisement.

It looks like you are using two “Full Description Contains” columns? Not sure it’s designed to do that (never tried). I would think you would need to instead use a regex. I’m not a regex expert, but Gemini suggests something like ^(?=.*Cash App)(?=.*Sylvia).*$ in a column called “Full Description Regex”. That would look for both “Cash App” AND “Sylvia” reguardless of the order they appear.

So I have a discovery here. I went ahead with CASH APP.*SYLVIA|SYLVIA.*CASH APP and this was working for AutoCat (Blanks). When I do AutoCat (Run Rules on All) the same thing happens, Sylvia is now categorized by keys.

This AutoCat (Blanks) works because it’s the first rule that hits in the AutoCat sheet.

AutoCat (Run Rules on All) doesn’t work because it’s the LAST rule that works therefore the general Cash App rule is applied.

For the Key category, shouldn’t there be a Locksmith in the 2nd Full Description Contains? Otherwise, that rule is going to change every transaction the contains Cash App to Key.

Here are two rules I pulled from the help guide that I think apply:

Rule processing order
The rules are processed in a top down order, so put your most fine grained (specific) rules at the top of the sheet and broader (generic) rules lower down.

Run Rules on All option
If you choose to have it run on all transactions (including those that are already categorized) this will overwrite existing categorizations where a rule matches so use this feature carefully.

Any Cash App payment going out EXCEPT for Sylvia would be for Key. There’s other many name after Cash App that would be for keys.

I truly wish AutoCat would behave to where it stops on the first rule and not the last rule when choosing run rules on all

AutoCat is supposed to work top down. I am not sure if because you have 2 columns with full description contains if part of the problem or not. Have you tried this scenario with only one full description contains? Maybe part of the problem is that cash app is on both transactions, so it stops with the first one. Do you have any other auto cat rules with description like you are having an issue with? Also are you using sidebar fills or direct fills? I was looking to see some settings for auto cat, and with direct fills it doesn’t look like the settings are the same. Hopefully we can work through and get to the bottom of this. You always have the option of contacting support at support@tiller.com as well; they have access to see things and know more things than me.

My situation requires an AND use of AutoCat. All Cash app transactions that are negative polarity that are NOT Sylvia are “Key”.

I have confirmed that AutoCat (Blanks) does work with the first hit from the top down. AutoCat (Run Rules on All) stops at the last rule that is compatible which is why I have this issue. I’m going to start from scratch and this time never using autocat’s (Run Rules on All) anymore because of this rule. I don’t know if they’ll ever fix this in the future due to the way it’s designed.

@TheKeyMeister I think the two Description Contains columns is a factor here. Also something with the way the rules are configured and how your Description Contains text is entered. If you use CASH APP*SYLVIA for the rule higher in the list and then just CASH APP for the lower one it will still match correctly even when running on All. I just verified this in a test sheet. You could also just use the word SYLVIA as the Description Contains if that’s the only instance where the word Sylvia would appear in the description of your transactions.