Feedback and suggestions for Simplifi from a new user (multiple features)

Guided categorization flow

There is no clear guidance distinguishing transfers, payments, reimbursements, and income. This leads to incorrect categorization, double counting, and confusion in budgeting. A guided categorization flow (e.g., “Is this spending, a transfer, or a reimbursement?”) would improve accuracy and on-boarding.

Rules

Rules are not automatically suggested when categorizing transactions. Users must manually create rules after the fact, which leads to repetitive work and inconsistent categorization. A prompt like “Apply this to similar transactions?” or "Merge this rule with similar existing rule?" after categorizing would significantly improve workflow efficiency.

Transaction descriptions

Privacy.com masked transaction descriptions make it difficult to create reliable rules or recurring matches because identifiers are inconsistent and shared across merchants. This forces manual cleanup and reduces automation effectiveness. Improvements could include better rule logic (support for multiple conditions/AND filters) and a merchant normalization layer that locks user-defined names. 

Slight variations in transaction names by merchants or banks of amounts (such as masked Privacy.com descriptions or fluctuating utility bills) result in duplicate recurring entries instead of being grouped into one. This fragments tracking and requires manual cleanup. The system should use fuzzy matching (normalized merchant names, tolerance for amount variation) and allow users to merge recurring series. 

Spending Plan

There is no distinction between one-time large expenses and normal recurring spending. Large purchases (e.g., appliance replacement) distort category budgets and require manual exclusion each time. A useful feature would be a “one-time expense” flag that excludes transactions from recurring trends and optionally from the Spending Plan. 

Recurring setup

Recurring setup does not support variable dates properly. Selecting multiple days creates multiple charges instead of representing a single monthly event with a flexible date. This breaks common use cases like credit card autopay or manually scheduled payments. A better design would allow a “monthly, flexible date” option with a tolerance window. 

Recurring transactions and the Spending Plan are disconnected systems. Creating a recurring item does not automatically add it to the Spending Plan’s Bills section, which is counterintuitive and forces redundant manual setup. A fix would be to allow recurring items to be optionally auto-added to the Spending Plan or unify the models so recurring bills are recognized as budget items. 

When selecting transactions to create bills for spending plan, I can't move the column dividers to see the entire transaction name, so that I pick the correct most recent one.

There is no way to bulk manage recurring items (delete, disable, or edit). When many incorrect recurring items are created, users are forced to delete them one at a time, which is not scalable. This significantly degrades usability. Adding multi-select with bulk actions (delete, exclude from plan, mark as non-recurring) would resolve this. A fix I described earlier for better identifying relevant transactions to setup a recurring bill may correct this issue implemented properly.

Auto-detection of recurring transactions is overly aggressive, especially after importing historical data. It creates dozens of incorrect recurring entries from one-off purchases like gas stations or random merchants. This reduces trust in the feature and creates a large cleanup burden. A better approach would be to require a higher confidence threshold (e.g., at least 3 occurrences with consistent timing) before creating a recurring, and provide a setting to disable auto-creation from imported data.