Convert image to Visio diagram?

In practice, there are a few tools available to convert an image to a Visio diagram. One of them is Image Converter for Visio, which pretends to even be able to "Add connection points to shapes".

While I haven't personally tested such tools, I would be highly surprised if they would work for something other than the most basic situations. Not because of the reason mentioned by SecurityMatt¹, but because image to vector conversions are known for not working very well. Even Live Trace feature in Adobe Illustrator is not working perfectly well, while Adobe invested a huge amount of effort in this feature.

Images are not rendered perfectly well. For example, if we were exporting the same diagram, the images would not be identical at pixel level, for example because I have slightly changed the Clear Type options for my LCD screen. This makes the OCR of a diagram not obvious, not counting the fact that Visio diagrams can be customized by changing color, size, weight and other visual aspects of elements.

Visio can also embed ordinary images, which makes things even more difficult, especially if those images are acting as shapes (imagine having a network map where network devices are replaced from the ugly default ones available in Visio by some more graphical ones).

Conclusion: feel free to try the tool I referenced or similar tools, but don't expect magic from them.

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^{¹ It seems to me that the case illustrated by SecurityMatt would be extremely rare. If the arrow is joined up behind an element, there is something wrong with the diagram. Why would somebody do that? Isn't the point of a diagram to make it visually clear what is joined where?}