An OverflowException error occurs if you make the mistake of selecting multiple large numeric values while Show Grid Aggregates is enabled and SUM is checked. 80% of the tables in our database has a minimum of 1 NUMERIC(29,0) columns with values like 30579915573912992440587781562 (our GUID). If more than 1 value is selected when SUM is checked, an error occurs for each value. If only a few values were selected, you can usually click OK on the errors and return back to SSMS, but if ~15+ are selected it can cause SSMS to crash after clicking OK for the first ~10.
For now I try to leave SUM unchecked unless I explicitly need it, but when you're flying through queries it's easy to forget to uncheck it.
Build version: 3.7.7170.22827
Build date: 2019-08-19
SSMS version: 18.4
Windows 10 Enterprise (Build 18362.476)