Hi there Chris Brinkley,
I see that you are experiencing a bit of an issue with your iMac waking from sleep. I have an article for you with some suggestions for addressing this, and it can be found below:
Your Mac might pause a few seconds before it wakes up. If it doesn't seem to wake at all, check for these possibilities:
- Your screen brightness might be turned down.
- If you're using an external display, your display might be turned off.
- Your Mac might be in safe sleep. To wake from safe sleep, press the power button.
- Check for a sleep indicator light, if applicable, and make sure that your Mac isn't turned off.
These additional steps may help identify or resolve the issue:
- Reset the SMC.
- Reset NVRAM.
- Disconnect external devices other than your Apple keyboard, mouse, and display. If that resolves the issue, gradually reconnect your devices, testing each time, until you find the device that is interfering with sleep. Then check the documentation that came with the device, or contact the device manufacturer.
- Start up in Safe Mode to see if the issue is related to non-Apple startup items, login items, or kernel extensions.
- Try to isolate the issue by using another user account.
If your Mac doesn't sleep or wake when expected - Apple Support
https://support.apple.com/en-us/HT204760
Take care, and thanks for visiting the Apple Support Communities.
