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I retired at the end of May this year and I made 4 entries for in-year salary income for the first 5 months of the year as explained below. However, none of these are being reflected in Time Machine which is instead showing $0.01 under EXTERNAL INCOME for this year. There are no error messages.
 
For clarity, for each entry, I selected "Salary" from the drop-down.
 
Entry 1 is from Jan 1 to March 31 with annualized $ amount
Entry 2 is from April 1 to May 31 (to reflect salary adjustment and ending on retirement date) with annualized $ amount.
Entries 3 and 4 are both one-time entries: one for Bonus payout and the second for Vacation pay out. In each case, I entered the full respective $ amount and entered start date = end date.
 
I have tried deleting and re-entering all the data but nothing is working and Time Machine is basically behaving as if I have to pull all that money from my savings to pay for my expenses.
 
To be clear, this function used to work and I am only recently seeing this behaviour.
 
Note: I also made a 5th entry for a partial Bonus payout that will come in 2027 and it is apppearing correctly in Time Machine.
 
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Income entries that end prior to the date you run the TIME MACHINE will not be reflected in the reports as it reports only from today on. 
 
You used to see them because the end date was before today, and it would show whatever amount was from today to the end of this year. Now it's not shown because the income has ended. 
 
You are correct in entering those previous incomes as it still considers those incomes for tax purposes.
In the screens right before you run the TIME MACHINE, you should also enter the taxes and deductions you’ve paid year-to-date so it can credit you. If you leave that field blank, the estimate will be too low in this case, as the estimate is just a prorated value for the year, whereas all your income and taxes were paid early.  
 
It’s best to give it an accurate value for taxes deducted year date so it can credit you properly, which will reduce required withdrawals to pay the taxes. 
 
That should help, but let me know if you still have questions.