There are instances where the company does not meet the definition of a broker and has a reporting obligation to file Federal form 1099-DIV.
If a company does not meet the definition of a broker, it may still have a reporting obligation. Form 1099-DIV, Dividends and Distributions, is required to be filed when a company pays a shareholder $600 or more during a calendar year to liquidate all or part of their stock. The amount paid to acquire the shares would be reported on the 2019 Form 1099-DIV in Box 9, Cash Liquidation Distributions, if cash was paid, and/or Box 10, Noncash Liquidation Distributions, at fair market value of the property distributed or paid other than cash. Form 1099-DIV is required to be furnished to recipients by January 31 of the year after the year in which the transaction occurred.
However, you state that the 1099-DIV does not report an entry in box 9 of the 1099-DIV.
It sounds like the entry should be reported as sale of an investment on Schedule D Investment income / Stocks, Cryptocurrency, Mutual Funds, Bonds, Other. You would report a basis of $25 and sales proceeds of $50 and a capital gain.
However, I would contact your employer to see whether they have an explanation why the transaction was not reported in box 9 of the 1099-DIV.
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