I am struggling to figure out this issue. I format all my maps to have a 140x140 dpi resolution and configure the grid to be 2x70 per square. My tokens are all 280x280. Everything was working fine. When I drag a token to the map, it resizes to fit within the grid. I assigned a token to a character and drag that character onto the map and it resizes properly. Everything working as expected. I decided I wanted to change the token for an existing character. So I created a new 280x280 token and uploaded it. If I drag the token directly onto a map from the library, it auto-resizes just fine. However, if I update the token assigned to the character to this new token (which is the same size), it no longer auto-resizes when I drag that character onto the map. Here are a few things I tried... I created a brand new character and assigned it the new token. It auto-resizes just fine when dragged to a map from the journal. I updated the token on the brand new character. It continues to auto-resize just fine. I removed all tokens from a character that was having a problem and even the default token is not auto-resizing. Here is a reference for the attached image... A is the image copied directly to the map from the library. It auto-resizes exactly as expected. B is the image when I drag the character with this token from the journal to the map. It is the same image as A, but does not auto-resize. This is a character that already had an image assigned to it. I updated it with the new image as the token. (the original image was working fine, but if I now change the assigned token back to that original image it no longer auto-resizes) C is the image when I assign the token to a brand new character and then drag that character from the journal to the map. It auto-resizes just fine. I can even assign a different token to this character and it continues to auto-resize just fine. D is the default image when I remove the token from a character that was giving me problems and drag that character to the map. Even the default image is no longer auto-resizing. It seems that something has happened to the existing characters that has broken the auto-resizing of the tokens. Since this all works as expected except on these existing characters, I do not see this as a bug but rather something that must have changed in the config of those characters that is causing this result. I am at a loss figuring out where to look. If anyone has any thoughts on what I could look at, I would appreciate it.