Why is the second Auto-Match always needed?

Summary:

A very simple transaction matching with few transactions, just GL vs Bank with 1toMany rule, but it never got matched after the first Auto Match. After running Auto Match the second time, it got matched. How do I fix this?

Content (please ensure you mask any confidential information):

The rule conditions are Amount matches exactly, Transaction Match Value matches exactly.

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Code Snippet (add any code snippets that support your topic, if applicable):