A family of Microsoft word processing software products for creating web, email, and print documents.
The reason the "restart at 1 / continue numbering" buttons feel like they've gone missing is that on Mac, Word hides most of this behind the right-click menu, and the Windows-only "Set Numbering Value" command simply doesn't exist in the Mac version. So you're not imagining it.
A few things worth trying that go a bit further than restarting:
If a heading has jumped back to 1 but should keep going, right-click directly on the number itself (not the text) and pick Continue Numbering. On Mac that option only shows up when you click the number, which is easy to miss.
If you need a very specific number that the right-click menu won't give you, select just that heading, right-click, choose Bullets and Numbering, go to the Outline Numbered tab, click Customize, change the start number, and make sure "Apply changes to: Selected text" is set, otherwise it renumbers the whole document.
If numbers keep misbehaving no matter what you do, the problem is usually that your headings belong to several separate lists instead of one. Click in your first Heading 1, go to Home, click the Multilevel List button, then Define New Multilevel List, click More, and for each level set "Link level to style" to Heading 1, Heading 2, and so on. After that, you never touch the numbering buttons again; you just apply the heading style and the number follows automatically.
One more thing: a file that has been through Google Docs and back often carries broken list definitions that can't be repaired. The cleanest fix is to paste the text into a fresh Word document as unformatted text and reapply the heading styles there. It's a bit of work, but it is recommended as the one approach that reliably clears this kind of corruption.
Hope that gets your document back under control.