Old Toshiba laptop is needing replacement and this boomer is wondering what the easiest  way to transfer files to a new one. Any help will be greatly appreciated.

I think Winders has some kind of transfer program in there or there are probably many offered on software sites like tucows etc but really it is spring cleaning time. I am sure you have a ton of junk all over the place in there that needs to be organized and deleted.

You ned to figure out the method Windows uses to network the 2 together and just drag the useful stuff from the old one to the new one. Any service offered can't do that, it just drags all the data from one to the other, it doesn't know what needs to be tossed.

Fellow Boomer, what sort of files (and how many) do you need to transfer? If I were doing it, and there was too much stuff to shoot up to the cloud (or if you'd rather not do that), I'd pull the old drive, put it in an external drive reader (fairly cheap on Amazon) and just shoot them over to the new device via USB. That's how I generally do it at work. Assuming that you're not thinking of trying to move software over to the new device.

This is what I usually do but I have terabytes of data to move.  Also, back it up before you pull the drive because accidents happen.

Option 2 is to back it up to an external USB or NAS and just copy it to the new laptop.

Make sure you have saved all of your important documents to the appropriate folders.  Docs to the Documents folder.  Pictures to the Pictures folder.  Music to the Music folder.  Don't forget about configuration files.  It only took me 3 months to get my new work laptop working at 100% and finally retire the old one but it is definitely more complicated that the average user's laptop.  I was able to upgrade the hard drive in my my personal desktop in a few hours.  Going from a 500GB SSD to a 2TB SSD, the sector size difference stopped me from cloning the old drive.  I used the external drive reader option and just kept it connected to my PC.  Over the next few weeks, as I needed to complete tasks, I would install the needed software and search the old drive for a configuration file.  Copy it over and I was back in business.

honestly the least trouble is to have both the old and new laptop on your network, share the drive and transfer what you want that way.
will take longer than putting it in an enclosure or physically moving the drive to the new laptop, but it is probably free based on what you have already.

I would hard line both in as that will be faster than wifi, but just depends on what you are using. as some new laptops don't have network ports.

Copy your entire documents folder to some portable storage.

Copy that to the new machine.

Maybe also copy your entire Users folder as well.

Thanks it's mostly pictures when I think about it. Looks like I may just use the cloud to store them them download onto the new laptop.