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Hi Tania B,
If this functionality was working normally until recently and then stopped without any changes on your side, it may be related to a recent Outlook update, particularly since you're using the Microsoft 365 Insider channel.
To help determine whether this is a broader issue or something specific to your environment, could you please confirm:
- Are you using Classic Outlook for Windows or New Outlook?
- What is your current Outlook version and build number? (File > Office Account > About Outlook)
- Does the issue occur with all mail merges or only specific ones?
- Have you recently received an Office or Outlook update?
As an initial troubleshooting step, please try launching Outlook in Safe Mode (outlook.exe /safe) and test whether the Schedule Send option becomes available during the mail merge process.
Based on your description, this sounds more like a recent change or regression rather than an intentional configuration change, especially since the feature had been working reliably for months. If other users on the same build can reproduce the behavior, that would further indicate a product-related issue.
We look forward to your update.