Save for Web disappears. Works for first image, then it's gone "system cannot find the path specified"

Thanks for your help, so far!  Well, I reset preferences (AND restarted PC) — bupkis! Same result. First Save to Web OK, Second Save to Web “can’t find path specified”. It doesn’t matter whether a psd, tiff or jpg.

By the way, I don’t use actions either. Full disclosure, I’m no longer working for clients. Just me, and every image is treated somewhat differently…in Photoshop, that is. As I mentioned, most of the work is done (with masking mostly) in Camera Raw.  

And this inability to Save to Web (a quick process I’ve used for, dare I say, a decade, which I use to downsize for emails mostly) is a must to get back.

For now, I’ll blame Windows. Or the erratic weather. 

Is IS a puzzlement!  (Am I dating myself?)

At this point, I can only guess it’s a Windows issue. When isn’t it? I can “Save to Web” once. Then I have to close Photoshop, reopen, and Save to Web once again, etc. Maddening. Might have to reset preferences on an old version and see what shakes. 

I have never used scripts ...ever.

I understand, personally, I couldn’t use Photoshop without scripts (or even actions).

Here is a script from Adobe’s Jeff Tranberry, which converts the current file to sRGB, opens Save for Web, then steps back in history to the step before converting to sRGB.

// https://www.tranberry.com/photoshop/photoshop_scripting/scripts/sRGBs4w.jsx

// enable double clicking from the Macintosh Finder or the Windows Explorer
#target photoshop

// in case we double clicked the file
app.bringToFront();

main();

function main() {
	if ( app.documents.length <= 0 ) {
		alert("You must have a document open to Save For Web");
		return;
	}

	// Convert the Profile to sRGB
	app.activeDocument.convertProfile("sRGB IEC61966-2.1", Intent.RELATIVECOLORIMETRIC);



	// Run Save for web and fix the document state
	try {
		RunSaveForWeb();
		PreviousState();
	}
	catch (error) {
		if (error.number != 8007) // Don't report user cancelled errors.
			alert (error); //  + ":" + error.line);
	}




	// This is a function that restores the document to the original profile
	// by stepping back a step in the history palette
	function PreviousState() {
	var id50 = charIDToTypeID( "slct" );
		var desc7 = new ActionDescriptor();
		var id51 = charIDToTypeID( "null" );
			var ref1 = new ActionReference();
			var id52 = charIDToTypeID( "HstS" );
			var id53 = charIDToTypeID( "Ordn" );
			var id54 = charIDToTypeID( "Prvs" );
			ref1.putEnumerated( id52, id53, id54 );
		desc7.putReference( id51, ref1 );
	executeAction( id50, desc7, DialogModes.NO );
	}


	// This is a function that calls the Save For Web Dialog
	function RunSaveForWeb() {
		var id637 = charIDToTypeID( "slct" );
			var desc89 = new ActionDescriptor();
			var id638 = charIDToTypeID( "null" );
				var ref21 = new ActionReference();
				var id639 = charIDToTypeID( "Mn  " );
				var id640 = charIDToTypeID( "MnIt" );
				var id641 = charIDToTypeID( "Svfw" );
				ref21.putEnumerated( id639, id640, id641 );
			desc89.putReference( id638, ref21 );
		executeAction( id637, desc89, DialogModes.NO );
	}
}

Instructions for using this code:

1. Copy the code text to the clipboard
2. Open a new blank file in a plain-text editor (not in a word processor)
3. Paste the code in
4. Save as a plain text format file – .txt
5. Rename the saved file extension from .txt to .jsx
6. Install or browse to the .jsx file to run (see below)

https://prepression.blogspot.com/2017/11/downloading-and-installing-adobe-scripts.html

Have you tried resetting preferences (first backing up custom actions, brushes and other presets)?