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One of the latest Microsoft Outlook 2019 / Office365 updates caused the problem that Outlook no longer sends email signatures correctly: Images in signatures are no longer embedded. The recipient no longer sees images for this reason.
The following registry entries fix the problem. As an alternative, this .reg file can be downloaded here (the .txt extension must be removed after the download)
Windows Registry Editor Version 5.00 [HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\Options\Mail] "EditorPreference"=dword:00020000 "MinimalHeaderOn"=dword:00000001 "Send Pictures With Document"=dword:00000001