Chrome Version: 67.0.3396.99 (Official Build) (64-bit)
Chrome OS Version: 10575.58.0 (Official Build) stable-channel eve
Chrome OS Platform:
  - Google Pixelbook
  - Firmware Version: Google_Eve.9584.107.0
  - Customization ID: GOOGLE-EVE
Network info:
  - WiFi: PSK (WPA or RSN)
  - OnHub from TP-LINK

Steps To Reproduce:
(1) Buy a personal Google Pixelbook with a Google Pixelbook Pen
(2) Enroll device to corp
(3) Set up corp account as device owner
(4) Log out of corp account
(5) Add personal Google-account as a secondary device account.
(6) Log out of personal account
(7) Log in to corp account
(8) Ensure Google Keep is default notes app
(9) Take a screenshot (or tap stylus icon and use the capture functionality)
(10) Tap "Annotate Image" action of screenshot notification popup.
(11) Try to annotate. It works fine.
(12) Log out of device owner corp account
(13) Log in to personal Google-account
(14) Ensure Google Keep is default notes app
(15) Take a screenshot (or tap stylus icon and use the capture functionality)
(16) Tap "Annotate Image" action of screenshot notification popup.

Expected Result:
Google Keep opens with the image, like on the corp account, and I can annotate.

Actual Result:
Google Keep opens with a blank page, but I can annotate.

How frequently does this problem reproduce? (Always, sometimes, hard to
reproduce?)
100% reproducible.

What is the impact to the user, and is there a workaround? If so, what is
it?
- Start Google Keep manually
- Start a new note
- Click to attach image
- Select the screenshot image
- Now you can annotate

Additional notes:
It does not matter whether you tap on the stylus icon and select "Capture region" or "Capture screen" or whether you use the keyboard shortcuts to take screenshots.

Also, it of course does not work at all with multi-sign-in, since Android apps only work in the current main account.

Video attachments (shared with google.com accounts):
- Corp Device Owner Account - Working:
  https://drive.google.com/file/d/1y6rCMstlL4PC9xdcUJlARW0qczw0t51n/view?usp=sharing

- Personal Account - Not working:
  https://drive.google.com/file/d/19Lp2JJ5SNp2fUhjSmDxX8kwNcEEzq8Gr/view?usp=sharing
 

Chrome Version: 67.0.3396.99 (Official Build) (64-bit)
Chrome OS Version: 10575.58.0 (Official Build) stable-channel eve
Chrome OS Platform:
  - Google Pixelbook
  - Firmware Version: Google_Eve.9584.107.0
  - Customization ID: GOOGLE-EVE
Network info:
  - WiFi: PSK (WPA or RSN)
  - OnHub from TP-LINK

Steps To Reproduce:
(1) Buy a personal Google Pixelbook with a Google Pixelbook Pen
(2) Enroll device to corp
(3) Set up corp account as device owner
(4) Log out of corp account
(5) Add personal Google-account as a secondary device account.
(6) Log out of personal account
(7) Log in to corp account
(8) Ensure Google Keep is default notes app
(9) Take a screenshot (or tap stylus icon and use the capture functionality)
(10) Tap "Annotate Image" action of screenshot notification popup.
(11) Try to annotate. It works fine.
(12) Log out of device owner corp account
(13) Log in to personal Google-account
(14) Ensure Google Keep is default notes app
(15) Take a screenshot (or tap stylus icon and use the capture functionality)
(16) Tap "Annotate Image" action of screenshot notification popup.

Expected Result:
Google Keep opens with the image, like on the corp account, and I can annotate.

Actual Result:
Google Keep opens with a blank page, but I can annotate.

How frequently does this problem reproduce? (Always, sometimes, hard to
reproduce?)
100% reproducible.

What is the impact to the user, and is there a workaround? If so, what is
it?
- Start Google Keep manually
- Start a new note
- Click to attach image
- Select the screenshot image
- Now you can annotate

Additional notes:
It does not matter whether you tap on the stylus icon and select "Capture region" or "Capture screen" or whether you use the keyboard shortcuts to take screenshots.

Also, it of course does not work at all with multi-sign-in, since Android apps only work in the current main account.

Video attachments linked below.