Hi Albert Perez,
In Outlook for Microsoft 365 / Outlook 2016 / 2019, the built‑in holiday set that gets imported into Classic Outlook only covers Gregorian years up through 2026. Because of that, Jewish and Israeli holidays can appear to stop part‑way through December 2026, even though observances like Hanukkah continue later in the month. Re‑adding the holidays in Classic Outlook doesn’t extend that range.
It’s also important to note that Outlook on the web (Outlook.com) uses a different holiday calendar from the old imported list in Classic Outlook. That online holiday calendar continues beyond 2026 and often appears as a separate calendar.
To check how things are set up on your side, please look at the following:
In Outlook.com / Outlook on the web, open Calendar and navigate to a date in 2027. If holidays appear there, the online holiday calendar is working as expected.
- In Classic Outlook, check the left pane under My Calendars / Other Calendars and make sure the holiday calendar is selected.
- If you want the holidays to appear together with your main calendar, turn on both calendars and use Overlay view (right‑click the holiday calendar and choose Overlay, or drag it on top of your main calendar).
- If your main calendar still contains older, previously imported holiday entries, consider removing those older items to avoid confusion or duplicates.
If holidays appear correctly on the web after 2026 but Classic Outlook still stops around December 2026, that usually points to a local display or profile issue in Classic Outlook, rather than a problem with the holiday data itself. Testing in Safe Mode or with a new Outlook profile can help rule out add‑ins or profile corruption.
To help narrow it down, could you please confirm:
- Do the holidays appear in Outlook.com when you check dates in 2027?
- In Classic Outlook, do they appear when the holiday calendar is enabled and shown using Overlay view?
Please let me know if this proves useful to you, or if you would like further assistance.
I'm looking forward to your reply.
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