Historically, if we needed to share a file with family, clients, … we could simply attach it to an e-mail and life was good.
Over the years, as file sizes have grown and also certain security updates have been implemented attaching files to e-mails has become a little less of a solution, so how can we still get our files, programs, … to destination?
Outlook Blocking Files By Extension
If you absolutely want to stick with good old e-mail attachments, but are seeing the file(s) blocked, this is because Outlook looks at file extensions to determine if a file is potentially dangerous, or not.
You can see the list of dangerous, and thus block extensions by reviewing:

It’s actually funny because the blocked listing seems incoherent. They block MDBs, but not ACCDBs?! And many more similar cases. Don’t try to understand.
Unblocking File Extensions
There is a workaround! You can create a registry entry and exempt certain extensions so they are no longer blocked (I did this for database files – mdb, accdb, …, since this was by business).
There are websites with all the details, but the gist of it is that you need create a ‘Level1Remove‘ String Value registry entry in
HKEY_CURRENT_USER\Software\Microsoft\Office\XX.0\Outlook\Security
and then enter a semicolon separated listing of safe extensions. For example:
.mdb;.accdb;.mde;.accde;.accdr
Now, files with any of those files should now get through at your end.
This does not however address the issue at the other end and would require your recipients implementing this same registry hack.
Change the File Extension
Another workaround can be to zip the file(s) or rename the extension. So you could rename the file to a *.dat or *.txt and attach that, but this requires the recipient being capable of renaming it back to the proper extension at their end.
Now, these workarounds might get you around extensions being blocked, but does not address the issue of files being blocked due to their size.
Online Folders
One great solution is to simply create an Online Folder for sharing the file(s). Using a service such as One Drive, Google Drive, Drop Box, … you can upload your file(s) and then simply provide the recipient with a download link via e-mail.
I actually employ this technique a lot. I like to create a folder by client and then by project and give each client access to their folder. This way we have a common folder for providing materials back and forth.
Remote Connection Software
Another option can be to use software that enable you to share you PC and also transfer files. TeamViewer is an excellent example of this. You can remotely access another users’ PC and then easily transfer files.
Sadly, Microsoft’s Quick Assist still does not have this feature. Who knows maybe one day they’ll add it and we’ll have everything under the hood of the Windows OS.
Upload to A Website
Yet another workaround can be to use an FTP client to upload the file(s) to a web server and provide the recipient a direct download link via e-mail.
Some browsers (thinking of Edge with the SmartScreen Filter feature) may still block the download though. You can get around this by simply using an alternate browser of your choosing (FireFox, Brave, …) or you can deactivate the feature altogether if you so choose by following the instruction found at:

At The End Of The Day, Just Be Careful!
As always, be careful with what you download and open. Use your common sense and don’t just do things blindly.
Always be sure you know the source.
Were you expecting to receive a file?
It only takes a minute to validate that the link/file is legitimate by contacting the sender.
Don’t just blindly click on links and download files because they were sent to you. Don’t click on that Enable Content button if you don’t know, and/or trust, the source! Remember you are always better safe than sorry!