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This is happening to me too, except using a Mac (OS 10.11.6) and Word version 15.14. The plugin automatically re-installed with a Zotero Standalone update (5.0.25). I went through the troubleshooting steps (https://www.zotero.org/support/word_proces…
@dstillman thanks for suggesting database integrity. I tried that and no issues were found. I will try to be patient until v5.0 comes out.