# Autocat AI Suggest - can it handle paired transactions better?

**URL:** <https://community.tiller.com/t/autocat-ai-suggest-can-it-handle-paired-transactions-better/35293>\
**Category:** AI Workflows\
**Tags:** autocat, ai\
**Created:** [October 2, 2026, 8:51pm UTC](https://community.tiller.com/t/autocat-ai-suggest-can-it-handle-paired-transactions-better/35293 "2026-10-02T20:51:05Z")\
**Posts on this page:** 3\
**Page:** 1

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**Author:** ![mhanson](https://sea2.discourse-cdn.com/flex020/user_avatar/community.tiller.com/mhanson/32/26143_2.png) [@mhanson](https://community.tiller.com/u/mhanson)\
**Post date:** [October 2, 2026, 8:51pm UTC](https://community.tiller.com/t/autocat-ai-suggest-can-it-handle-paired-transactions-better/35293/1 "2026-10-02T20:51:05Z")

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I notice that Autocat AI Suggest has a hard time with dividend + reinvestment transaction pairs. These typically occur exactly in pairs, with a credit and a debit for exactly opposite amounts and identical description fields, in the same account.

I understand the current scope of Autocat is only a single row so it’s tricky to find these (especially since they are not 100% guaranteed to be adjacent in the ledger, though they are always close). Does anyone have a clever technique for autocategorizing these?

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**Author:** ![jpfieber](https://sea2.discourse-cdn.com/flex020/user_avatar/community.tiller.com/jpfieber/32/4791_2.png) [@jpfieber](https://community.tiller.com/u/jpfieber)\
**Post date:** [October 3, 2026, 2:07pm UTC](https://community.tiller.com/t/autocat-ai-suggest-can-it-handle-paired-transactions-better/35293/2 "2026-10-03T14:07:41Z")

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I have an autocat rule that does “Institution Contains”, “Full Description Contains” and “Amount Polarity” (Positive or Negative) to tell them apart and then categorizes them accordingly.

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**Author:** ![ctlee](https://sea2.discourse-cdn.com/flex020/user_avatar/community.tiller.com/ctlee/32/7831_2.png) [@ctlee](https://community.tiller.com/u/ctlee)\
**Post date:** [October 6, 2026, 12:37am UTC](https://community.tiller.com/t/autocat-ai-suggest-can-it-handle-paired-transactions-better/35293/3 "2026-10-06T00:37:32Z")

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you’ll know best as each institution codes it’s dividends and purchases differently. But for a tax purpose, unless in a tax deferred account, it’s no different than you got the dividend and then you took that cash and bought more stock.  
i have auto cat first by institution as then how it usually codes the dividend and that is treated as income. and the stock purchase as either a wash (in cash terms) or just an increase in holdings.