Agreed. I need to replace with retouched images and have to reimport and scale each one.

when the image is updated in the source XD should ask if the image in the file should be updated with the new one similar to adobe illustrator. This way the workflow will be consistent.

I did not know you could drag an image onto an existing one. It should be a little more obvious. You could just add the option in the right click menu for dinosaur computer users.

In the design mode when customising pages where you'd like to have multiple similar pages, it would be very good to have a change picture or replace image option in the right-click section!
Just an idea

Agreeded, sometimes we have the same image imported differently in the file, it would be awesome to have a feature of automatic update like in indesign.

I so agree (works really nice in indd) - something like that, or maybe nested instead.

It would be nice if you could replace en image through right-clickin the image, and choose a new with the same maskings/placing browsing (instead of having to drag'n drop/having many windows on top of each-other)

further clarification: It would be nice to be able to drag an object (smart object, vector, image, symbol, etc.) onto an existing object that is linked into the prototype, and have that new object absorb any of the relevant properties/links that the old object had

It would be really nice to be able to replace an image/button/object (with all of its prototype links intact) with a symbol from the new symbol library.

There are three needs here.

First, here's the situation of how dealing with images in XD currently works:

On one hand we have the behavior from when we create a shape and drag an image into it. When we do this the image centers in frame at 100%, cropping anything outside the frame. As we change the dimensions of the frame, the image auto responds to fill 100%. This is great because that's how most images will be developed to behave online, so we can see and test the flex of images. BUT this only matters if we've already figured out how we want our images to crop.

So, then there is the second method of dragging an image into an artboard, drawing a shape over the top of it and using it as a mask. Double click allows us to position the image as we please. As we adjust the image frame it forces the visible area to stay visible, and anything that was cropped stays cropped. Every time we adjust the frame, we need to reposition the image (if our intent was to show more of it.) If we want to replace the image, we can drag a new one over the top and drop it it, BUT this crops our new image to match the dimensions of the original image, which is no good!

So here's what we need:

1) We need to be able to replace a masked image without cropping it to the original image dimensions. We need to have all the image real estate available to us as possible, to position the image as we please. Without this, we have to go through the whole mask an image process over and over again. I think InDesign is the best example of how this should work. It's a simple drag and drop action, which is way nicer than going through the whole "create a mask" process. It also has "fill frame proportionally", "fit content proportionally", "fit content to frame", and "fit frame to content" quick commands which are all super valuable in a workflow.

2) We need the ability to switch between how an image will behave inside an image frame.
Sometimes we'll need the flexibility to move things around. Once we have a final piece of artwork ready, we might want it to auto fit 100% like it will online. A simple set of buttons in the side panel could be enough to jump between these modes.

3) We need the ability to output an image crop to create a final piece of artwork that we can then immediately update to the auto fit 100% mode.

I could see two paths being helpful...

1. Copy an image/icon/whatever from another program (Illustrator is what I've tried). Select the image you want to replace in XD. Paste the image to replace the current XD image. Ideally it would maintain the dimensions of the previous image.

2. Select the image you want to change in XD. Have an option in the "Appearance" area to "replace image" and select from the Finder/Explorer.

The way I experienced this was using an Illustrator file with multiple Icons. If I try to drag one Icon out of Illustrator into XD, it doesn't work how I'd want to make it fast and simple.

I just tried to drag an .ai file from my desktop into my XD file and it did nothing.

I dragged an image from the Finder into the XD file, but it laid the new image on top of the current rather then replacing it.

How else can I help?

Yes please to this