Problem I have never had before.

[RClary]

Hi all, I am new to this forum, and I am having trouble associating files to a couple of programs. One is RWtools and the other is Winrar.   Every time I open a file with either program, I am always asked to chose a program to open them with, whereas in the past on my old computer, I could permanently associate the files with the programs.    I have been searching the internet for a solution but nothing is helping.  There was once suggestion to look at the program in regedit to see if the path is correct, and in either case, the programs paths were correct.  Is there anyone that knows of a possible solution. My specs are.

Windows 10 home 64 bit
Processor Intel Core i7-8700k 3.7 ghz
Ram 16 gig
Graphics Geforce GTX 1080ti

[DaveLembke]

So there is no checkbox to tell Windows 10 to remember?

You should see like at this link here in the how to a check box to always associate by file extension type to the programs you want. https://windowsinstructed.com/how-to-reset-file-associations-in-windows-10/

[RClary]

There is a check box, but that doesn't keep the file associated to the program.

[DaveLembke]

Are these older versions of these programs that were created before Windows 10 came along? It sounds like Windows 10 file association is broken for these programs possibly because Windows 10 doesn't support them for file association but that they are supported to still execute and run because 32-bit program support.

If these are the latest editions of these that have Windows 10 support then it sounds like a corrupt install where it wont take the file association. What versions of these are you running?

[BC_Programmer]

Windows 10's mechanisms for managing File Associations have been broken since the 1803 Update; possibly earlier.

In Registry Editor, if you navigate to HKEY_CURRENT_USER\Software\Microsoft\Windows\CurrentVersion\Explorer\FileExts you will see file extensions listed. if you scroll down to .rar, and expand it, I'll bet there is a "UserChoice" key. This is the problem.

See what is supposed to happen is there is a setting that indicates the users choice for file to open (eg. the "Always open with this Program" checkbox), and the hash value ensures that if the setting is changed by a program, then Windows will know "oh, the hash doesn't match" and will ask you what program to use again. The problem is that as mentioned, the Dialog is broken; it either doesn't set the UserChoice settings, doesn't set the Hash and can constantly ask you over and over even though you check it off each time.

The "solution" is to delete the key for the file types in question from that UserChoice key. Without that setting Windows will instead fallback to standard File associations and will open it with the file directly associated with it.

Note that if you use the Open With dialog with the file type, it is likely that this will "break" the file association again and it will begin prompting constantly.

[RClary]

Windows 10's mechanisms for managing File Associations have been broken since the 1803 Update; possibly earlier.

In Registry Editor, if you navigate to HKEY_CURRENT_USER\Software\Microsoft\Windows\CurrentVersion\Explorer\FileExts you will see file extensions listed. if you scroll down to .rar, and expand it, I'll bet there is a "UserChoice" key. This is the problem.

See what is supposed to happen is there is a setting that indicates the users choice for file to open (eg. the "Always open with this Program" checkbox), and the hash value ensures that if the setting is changed by a program, then Windows will know "oh, the hash doesn't match" and will ask you what program to use again. The problem is that as mentioned, the Dialog is broken; it either doesn't set the UserChoice settings, doesn't set the Hash and can constantly ask you over and over even though you check it off each time.

The "solution" is to delete the key for the file types in question from that UserChoice key. Without that setting Windows will instead fallback to standard File associations and will open it with the file directly associated with it.

Note that if you use the Open With dialog with the file type, it is likely that this will "break" the file association again and it will begin prompting constantly.

The Winrar program is a few years old, but worked on the old machine that ran Windows 10.  The other program is called RWTools with is used for editing video game called TS2019, and it is the latest version of the software. 

[RClary]

Windows 10's mechanisms for managing File Associations have been broken since the 1803 Update; possibly earlier.

In Registry Editor, if you navigate to HKEY_CURRENT_USER\Software\Microsoft\Windows\CurrentVersion\Explorer\FileExts you will see file extensions listed. if you scroll down to .rar, and expand it, I'll bet there is a "UserChoice" key. This is the problem.

See what is supposed to happen is there is a setting that indicates the users choice for file to open (eg. the "Always open with this Program" checkbox), and the hash value ensures that if the setting is changed by a program, then Windows will know "oh, the hash doesn't match" and will ask you what program to use again. The problem is that as mentioned, the Dialog is broken; it either doesn't set the UserChoice settings, doesn't set the Hash and can constantly ask you over and over even though you check it off each time.

The "solution" is to delete the key for the file types in question from that UserChoice key. Without that setting Windows will instead fallback to standard File associations and will open it with the file directly associated with it.

Note that if you use the Open With dialog with the file type, it is likely that this will "break" the file association again and it will begin prompting constantly.

I checked all the file extension I am having trouble with, including the rar extension, and none of them have the "UserChoice", key. 

[RClary]

I should say that all of the files that are not associating with winrar and rwtools, are in the Train Simulator 2019 game. They are specifically files with the exstensions, .ap, .proxyxml, .proxybin, .bin.  I used to successfully associate the .ap file with winrar, whereas the other files would associate with the rwtools program.

[RClary]

I solved the issue by updating to Windows version 1809.  And no, I never had the issue where that version deleted files.