Issues with transfers linking incorrectly

I don't know the best solution to ensure appropriate linking of transfers while avoiding incorrect associations; however, implementing a date comparison or constraint could be beneficial, as transactions from different years (e.g., a 2025 transaction and a 2023 transaction) should not link automatically. Some issues may be related to manual transactions or accounts that have been added for various reasons. While I cannot definitively confirm that all issues in recent months are tied to manual transactions or accounts, a majority of them likely are. Improved prompts during manual transaction edits—for example, options to confirm if transactions should be linked or unlinked to specific offsetting entries—could help reduce such errors. This approach would be similar to current prompts for linking reminders to transactions.

Other recent examples of linking issues include:

1) See my comments dated 5/13 & 8/20 on the post Handle Linking and Categorizing Transfer Transactions Better (edited) — Simplifi. In the 8/20 example, a $200 transfer was reported missing; the initial transaction was likely entered manually and was not a transfer. I suspect the original transaction was later linked incorrectly to an edited $200 transfer, although no transaction with the original downloaded description could be found despite reviewing several months' worth of $200 transactions.

2) In early August (8/16?), I added a new $40 transfer manually to a manual account and set the category to the downloaded bank account. I did this manually because it was a weekend, I typically review my finances over the weekend, and my bank doesn't include pending transactions in download or post over the weekend. The manual $40 transaction was incorrectly linked to a July transaction (7/27) (not a transfer) in the downloaded account instead of creating a new offsetting entry. In this case, I deleted the manual transaction I had just created, which changed the July transaction to Uncategorized rather than reverting to its previously selected category. Re-creating the transaction starting from the downloaded account resulted in correct behavior, whereas initiating it from the manual account led to incorrect linking.

Thank you for considering this issue.

UPDATE: I was able to resolve the original issue as noted in my previous comment. I did get screenshots before I made any changes today and did a screen recording while resolving the error. I don't want to post either here, but am happy to share directly with support as needed.

ANOTHER EXAMPLE OF ISSUE: I just created a new manual transaction/transfer between two bank downloaded accounts (again for $100.00) and it linked incorrectly as well. I entered the other account as the category when creating the original transaction (rather than leaving uncategorized and adding a second manual transaction like I did to fix the prior example). The 8/30/2025 transfer is showing linked to a manual transaction dated 7/31/2025 that was not listed as, nor should it be, a transfer. I'm going to resolve this in similar fashion to the original issue, but as you can see this is a recurring issue and I'm experiencing it with nearly every transfer that I am manually adding or editing.

@DryHeat I apparently didn't save a screen shot of that second example, but I believe in that case the 7/31 transaction remains manual. I have created a "workaround" to create "transaction registers" for my savings goals. Since I keep some of my savings goal funds in my primary checking account due to better interest rates, I create offsetting manual transactions in the downloaded checking account so I can better track my savings goals. So, this situation is definitely a unique use case.

As I noted in a reply on the below post, I do think the issues are more prominent when adding or editing transactions manually, and even more prominent when at least one side of the transfer is a manual transaction. I think my issues are even more complicated because I imported my historical transfers incorrectly and did a lot of "manual" transactions for the offsetting transactions to correct the historical data.

Now that I've been using the system for almost a year and have experienced the same issues on new transactions that had nothing to do with the original import issues, I'm confident there are gaps in the transfer matching/linking programming as there don't seem to be any/correct date or category limits.

Ultimately, like you, I haven't been able to clearly identify or understand the behavior and when it works as expected and when it doesn't. But this is definitely one of my biggest frustrations and trust issues with this system.