Attempting to update manually modified citation.

[Exception... "The operation couldn't be completed. (OSStatus error -1708.) @[displayAlert:document.m:188]" nsresult: "0x80004005 (NS_ERROR_FAILURE)" location: "JS frame :: file:///Applications/Zotero.app/Contents/Resources/extensions/zoteroMacWordIntegration@zotero.org/components/zoteroMacWordIntegration.js :: checkStatus :: line 405" data: no]

There's an edited citation in the document, with a removed period. That may have been accidental, but in case not, you should always avoid editing citations in the document if possible — you would want to fix the metadata, fix the citation style, or customize the citation, depending on the problem. Manual editing shouldn't break your document, though — normally it would just prompt you about whether you wanted to keep your changes and prevent further updates to the citation. But in this case the confirmation dialog is failing to show for you, which is why this is failing.

Restart Zotero and Word and try again. It may help to make sure Zotero remains visible on the screen — at the moment, if Zotero is completely hidden behind other windows, macOS can slow the app down significantly such that there's a timeout before the dialog is displayed, resulting in an error.

You can also follow the last step on Troubleshooting Errors in Word Processor Documents to isolate the problematic citation in a copy of the document, and then fix the citation in the original document. (To revert a modified citation, click on it and click Add/Edit Citation, which will prompt you to revert it.) There may be more than one modified citation in the document.

If nothing at all happens (i.e. you don't get errors or dialogs), look through all open Zotero windows, sometimes a citation dialog gets burried under other windows. If it isn't there restart Zotero and try again. Also see the troubleshooting instructions linked above.

Unless you can no longer even insert a citation into a new, empty document, you'll need to follow the last step on the page linked above to debug this. It explains how to isolate the problem so you can work around it and provide us with a document excerpt that we can use to try to fix any underlying bugs.

If you don't get any response from the buttons in a new, empty document after restarting your computer, see No Response from Plugin.

@dstillman thank you, I will update and hopefully it will work now!