No, it is not possible to set an initial value for a <input type="file" /> element. The reason for this constraint (which is enforced by the browser, not by ASP.NET) is security. Consider the consequences of a malicious website owner placing the following in a form:
<input type="file" value="c:\bank\secret.key" />
However, I am not sure that this limitation is really a problem in the scenario you are describing. Having the
<input type="file"> prefilled with the path to the image file on the server, is unlikely to help anyway, as the value selected in a file field is used to point to a file on the client, which will be uploaded as part of the form postback.
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