| Go to Start > Run > type cleanmgr
/sageset:50 . Ensure there is a space between cleanmgr and / > click
OK

In the resulting screen, choose your options by checking the
boxes. I choose all but the bottom two, and I did NOT check off Office
Setup Files.
Click
OK

Doing the above tells Disk Cleanup what we want it to do!
Now, let's tell our PC when to do what we want.
Go to Start >
Control Panel > Scheduled Tasks > Add Scheduled Task
> the Scheduled Task Wizard will appear, click Next.

Scroll down
until you see Disk Cleanup, click on it once to highlight it and click
Next

Here you will pick a name for the task, Disk Cleanup is fine.
Pick how often you want the task to run. I recommend Weekly or Monthly,
especially after running your automated CHKDSK! Click Next

Choose a
time and day, if necessary. Make sure the time doesn't conflict with any other
scheduled tasks, such as your automated CHKDSK! I run my your automated
CHKDSK on the first of each month, so I selected to run Disk Cleanup on the 2nd.
Click Next.

Note: Since Windows Update on my machine(s)
is(are) scheduled for 3AM, I tried to avoid scheduling anything that would
conflict with these sometimes critical updates. And, since I get up at 5AM, I
adjusted the start time for these scheduled events so I wouldn't have to wait
for them to finish. That is, after all, the whole point of scheduling these
things. ;-)
Here you will enter the user name and password that will run
the task. I selected my administrator account. (You must enter the
correct password!) Click Next.

Verify that your
settings are correct.
Check the box next
to Open advanced properties for this task when I click Finish, and then
click Finish

In the resulting screen you should only have to type
/sagerun:50 at the end of the Run line. Ensure there is a space between
.exe and /.

Click Apply.

Enter your password. Click
OK to close out the 2 screens.
Now, let's just suppose you want to
verify that we've done this correctly.
Go to Start > Control Panel > Scheduled
Tasks and make sure your task is there. Right-click on it and select
Properties to verify and/or make any changes.
That's it! Your task will now run automatically!
(Many thanks to TweakHound)
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