I cannot reproduce this behaviour. I set `Send error reports to Canonical` to 
`Automatic` and it worked on my noble laptop:
```
$ ls /var/crash/ -1
_usr_bin_divide-by-zero.1000.crash
_usr_bin_divide-by-zero.1000.upload
_usr_bin_divide-by-zero.1000.uploaded
```

Can you share the journal log during your tests?

** Changed in: apport (Ubuntu)
       Status: New => Incomplete

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https://bugs.launchpad.net/bugs/2065290

Title:
  apport does not write .upload file in case of Automatic send

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