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I have found often with this type of behavior going from an old OS to Windows 10, problem is often related to security. Even running as Administrator does not always give you access to write. In the past creating the destination folder and adding explicit permissions to the account to have full control and turning off inheritance makes a difference. Given the age of the code there may be missing com objects or DLLs that are no longer part of the Windows 10 OS. These problems are a bear to resolve but with the correct tools you'll learn what's generating the error.
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It sounds as if you are dealing with two separate products: a custom "line of business" program written by someone who no longer wants to support it, and a packaged barcode/label making program. Or is it just multiple custom programs that form the "line of business"?
It sounds like the label product installed, but did not create two desktop icons see was expecting to see. It is a bit vague on exactly when the two files are supposed to be created: is it after the software is installed or is one part of the "line of business" software generating those two files which she clicks on and the label software is supposed to utilize?
It is just a slow and steady process to determine her problem, and you indeed might end up with "sorry, there is no solution." How important is this client? Can you skip a lot of the determination work and just get to "sorry" earlier?
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Old programs work better if NOT installed under C:\Program Files (x86).
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Found this that may be fairly easy to figure out what it's trying to create.
There are other solutions too for tracing file access.
It's may be failing the file creation as it's using a on-existent path and hopefully this software sees the failure.
https://www.visualclick.com/content/cptrax-for-windows-active-directory.htm
Or process monitor should do it too
http://technet.microsoft.com/en-us/sysinternals/bb896645.aspx
You can run it directly from the site if you want
http://live.sysinternals.com/Procmon.exe
Mike
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For "app data", the usual convention is:
c:\ProgramData\<company>\<app data="">
(i.e. "Users" is not the only place where app data gets stored; including the "exe folder").
"(I) am amazed to see myself here rather than there ... now rather than then".
― Blaise Pascal
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I would run the program in a VM of Windows 7, and use the old SysInternal Tools to identify the file creation.
I have had THESE kinds of problems when going to Windows 8 and Windows 10 from very old code that writes stuff to it's own PROGRAMS folders... ALL due to security differences.
Windows DOES NOT want things written "anywhere", data goes in appdata, etc.
And running as Admin does not always fix stuff, because the resulting EXPLORER instance is NOT in admin mode, so it may not see the files created.
That is the FINAL nail in the coffin. If it is using ANY KIND of share, KNOW THIS: A share created with an ADMIN account is NOT accessible to the USER account, AND VICE VERSA. This crushed us recently on a VM setup where the developer runs as admin, but the use program cannot. AND BAM, the share can only be accessible by one at a time, until you tweak the registry!
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Get a copy of ProcessExplorer from sysinternals.com. It's free:
Process Explorer - Windows Sysinternals | Microsoft Docs[^]
This program is extremely handy--it will show you every file that is being created/read/etc, along with what registry keys are being read/added/etc. The log files get huge fast, but for a tricky job like this it will be worth its weight in gold. It's helped me track down really weird/obscure stuff like this.
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I'd upvote every suggestion that the program is trying to write files in a now restricted space. There are so many butts running around with chunks taken out of them by this security change, mine being one of them. It's an easy change if you have the source code - muahahaha - don't comment on that. As a consultant, I'd say sorry, your code is obsolete, here are some options and here's what it will cost you. Let me know if I can help.
Charlie Gilley
<italic>Stuck in a dysfunctional matrix from which I must escape...
"Where liberty dwells, there is my country." B. Franklin, 1783
“They who can give up essential liberty to obtain a little temporary safety deserve neither liberty nor safety.” BF, 1759
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Dunno if someone mentioned that already, but Process Monitor is a fantastic tool and is well-suit for exactly this use case.
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Spot a clue in unusual theory (11)
Sent from my Amstrad PC 1640
Never throw anything away, Griff
Bad command or file name. Bad, bad command! Sit! Stay! Staaaay...
AntiTwitter: @DalekDave is now a follower!
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Hmmmm... maybe attempting these everyday is finally starting to pay off!
Speculation = theory
Anagram of Spot a clue in
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Well done - you are up tomorrow! 
Sent from my Amstrad PC 1640
Never throw anything away, Griff
Bad command or file name. Bad, bad command! Sit! Stay! Staaaay...
AntiTwitter: @DalekDave is now a follower!
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Finally! A decent replacement for Javascript! 
Latest Article - A Concise Overview of Threads
Learning to code with python is like learning to swim with those little arm floaties. It gives you undeserved confidence and will eventually drown you. - DangerBunny
Artificial intelligence is the only remedy for natural stupidity. - CDP1802
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Well, the BASIC interpreter is implemented in js.
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I hated BASIC the first time around already. JS too, as I dislike interpreters in general. Now, what would you expect me to say to this interpreted interpreter?
I have lived with several Zen masters - all of them were cats.
His last invention was an evil Lasagna. It didn't kill anyone, and it actually tasted pretty good.
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CodeWraith wrote: Now, what would you expect me to say to this interpreted interpreter?
Two wrongs make a right? 
Latest Article - A Concise Overview of Threads
Learning to code with python is like learning to swim with those little arm floaties. It gives you undeserved confidence and will eventually drown you. - DangerBunny
Artificial intelligence is the only remedy for natural stupidity. - CDP1802
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Marc Clifton wrote: Two wrongs make a right?
No, that's three lefts.
Michael Martin
Australia
"I controlled my laughter and simple said "No,I am very busy,so I can't write any code for you". The moment they heard this all the smiling face turned into a sad looking face and one of them farted. So I had to leave the place as soon as possible."
- Mr.Prakash One Fine Saturday. 24/04/2004
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Two wrongs? Really?
Start counting[^]. After that we shall pluck apart good old BASIC.
I have lived with several Zen masters - all of them were cats.
His last invention was an evil Lasagna. It didn't kill anyone, and it actually tasted pretty good.
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Or two wrongs make a write?
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CodeWraith wrote: Now, what would you expect me to say to this interpreted interpreter?
They cancel each other out?
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That's what Dumb also always says when he executes Dumber's next master plan. The scary thing is how many actually believe it besides him.
I have lived with several Zen masters - all of them were cats.
His last invention was an evil Lasagna. It didn't kill anyone, and it actually tasted pretty good.
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I am an ostrich
Latest Article - A Concise Overview of Threads
Learning to code with python is like learning to swim with those little arm floaties. It gives you undeserved confidence and will eventually drown you. - DangerBunny
Artificial intelligence is the only remedy for natural stupidity. - CDP1802
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