I found that this was also reported in Jan 2025 by someone, but they didn't respond with more details when asked.
This is how it looks to me:
Simplifi CSV Import — Category with "/" Not Recognized
When importing a CSV transaction where the Category field contains a / character (e.g., Services:Professional/Business), Simplifi fails to match it to the existing category of the same name. Instead of applying the category, Simplifi sets the transaction to Uncategorized and places the category string in the Notes field prefixed with Category: (e.g., Category:Services:Professional/Business).
Steps to reproduce:
- In Simplifi, create or confirm a category named
Services:Professional/Business - Create a CSV with a transaction row where the Category column is
Services:Professional/Business - Import the CSV into Simplifi
Expected: Transaction is categorized as Services:Professional/Business
Actual: Category is set to Uncategorized; Notes field contains Category:Services:Professional/Business
Workaround: Rename the category to avoid / — replacing with & resolves the issue and imports correctly.