Do previously specified lot assignments survive the Windows→Mac conversion?

QFan8471

I'm a long-time Quicken Classic Business & Personal (Windows) user evaluating a move to Quicken Classic for Mac. Before committing to a one-way conversion, I converted a copy of my file and have been testing it against the Windows original.

Good news first: the Mac version does support specifying lots. The "Specify Lots Assigned in This Transaction" dialog is there, with Auto Select (FIFO) plus manual per-lot share entry. That resolved my biggest concern going in, since several older threads claim Quicken Mac is FIFO/LIFO only.

My question is about history, not the feature itself.

In Windows I have deliberately specified lots on a number of past sales — non-FIFO selections made for tax reasons. After conversion, those sales on the Mac side do not appear to retain those specifications; they present as FIFO.

I've seen it explained (in a Windows context) that when no lot specification exists for a sale, Quicken computes FIFO dynamically against whatever lots are currently available, rather than storing an assignment. If that's also true on Mac, my working theory is that the converter carries the transactions but not the lot-specification records, so every historical sale falls back to dynamic FIFO.

What I'd like to know:

1. Is this expected behavior for the Windows→Mac conversion? I don't see lot assignments listed among the known conversion losses (invoices and attachments are documented; lots are not mentioned).
2. If it is expected, is it documented anywhere I've missed?
3. Is there any approach short of manually re-specifying every historical sale? I'm aware of the Remove Shares / Add Shares and Shares Transferred techniques for rebuilding basis, but with years of history that isn't realistic.

Why this matters: if historical lot assignments silently revert to FIFO, realized gain/loss and holding-period math diverge from both my Windows file and my brokerage's 1099-B — and it does so quietly, since nothing looks broken. It only shows up on the sales where I'd deliberately chosen non-FIFO lots.

Happy to provide specifics from my test file. If someone can tell me this is a settings issue or that I've tested it wrong, I'd genuinely welcome being corrected — I'd like to make this move.

Quicken Classic Business & Personal (Windows) — Version R68.28, Build 27.1.68.28 on Windows 11 Home
Quicken Classic for Mac — Version 9.0.3 (Build 900.60651.100) on macOS 26.5.1, Apple Silicon

Quicken Kristina

Hello @QFan8471,

Thank you for reaching out. Apologies for the slow response. I didn't receive any notification about this post.

Unfortunately, historical lot assignments do not survive the conversion process.

I don't see it specifically listed in our documentation as information that carries over or as information that is lost. The closest one I can find is this article: https://info.quicken.com/mac/what-data-gets-carried-over

Data that is carried over:

• Accounts
• All transactions
• Scheduled transactions
• Categories
• Classes and tags (these are both called “tags” in Quicken)
• Loan details

Data that is not carried over:

• Online banking download setups: If you’ve set up accounts to download data from your financial institutions into your Quicken for Mac or Quicken for Windows data file, the information about your financial institutions and your user ID is typically carried over to Quicken. However, additional setup may be required, such as providing passwords to make everything work correctly.
• Custom reports: Quicken does not import any custom reports created in your old data file.
• Online banking passwords: You need to re-enter your passwords the first time you update your accounts in Quicken.
• Attachments
• Budgets
• Data from the more advanced features is not carried over. For example: business data, rental property data, lifetime planner data, cash flow forecast data, spending plan data, debt reduction data, emergency tax records data, tax planner data, and home inventory manager data are not carried over.

You can select the default behavior on an account basis, but that would apply to newly downloaded information, not to information that's already in the account. For more information, please see this article: https://info.quicken.com/mac/selling-securities#Default-lot-assignment

I hope this helps!