Generating image sizes when uploading through wp.media

Verify that the “GD” php library is enabled. You can do so by adding phpinfo(); to one of your php templates and then search the result for GD or GD Support.

The GD library is used for image manipulation and resizing is one of those functions.

To enable GD on windows you can edit the php.ini file in your php installation and uncomment
the php_gd2.dll extension:

; Windows Extensions
; Note that ODBC support is built in, so no dll is needed for it.
; Note that many DLL files are located in the extensions/ (PHP 4) ext/ (PHP 5)
; extension folders as well as the separate PECL DLL download (PHP 5).
; Be sure to appropriately set the extension_dir directive.
;
;extension=php_bz2.dll
;extension=php_curl.dll
;extension=php_fileinfo.dll
extension=php_gd2.dll ; <-- THIS ONE
;extension=php_gettext.dll

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