calamity@, does this ring any bells? 

Interesting, this isn't quite the bug I was expecting. Just to be clear, do both device A and B have access to the web site and it's associated icons?

Yes, as mentioned both devices are on the same local network and have access to the web app and its icon. This is also shown by the fact that I was able to add the app including the correct icon on device B after deleting it first (from device A which then synced the deletion to device B).

Please keep in mind the mentioned pitfall as after this second test on device B the correct icon also reappeared on device A. Apparently it is fetched from the local cache in this case. I think that's the case because I actually also have a device C in the local network which still has the generic icon after quietly syncing the apps from both tests.

Just let me know if I can help in any way (e.g. with net-internals logs).

OK thanks. Some more info that will help:
1. After adding the app and before it is synced to another device, go to chrome://sync-internals/
2. Select the "sync node browser" tab
3. The app should be listed under "Apps"
4. Please share the SPECIFICS field contents for the app. It should be something like:

 {
    "app": {
      "app_launch_ordinal": "zzzzzzzzzzzz",
      "bookmark_app_icon_color": "#F0B310",
      "bookmark_app_url": "https://keep.google.com/",
      "extension": {
        "disable_reasons": "0",
        "enabled": true,
        "id": "hcfcmgpnmpinpidjdgejehjchlbglpde",
        "incognito_enabled": false,
        "installed_by_custodian": false,
        "name": "Keep",
        "remote_install": false,
        "update_url": "",
        "version": "0"
      },
      "launch_type": "WINDOW",
      "linked_app_icons": [
        {
          "size": "16",
          "url": "https://ssl.gstatic.com/keep/keep.ico"
        },
        {
          "size": "17",
          "url": "https://ssl.gstatic.com/keep/icon_16.png"
        },
        {
          "size": "32",
          "url": "https://ssl.gstatic.com/keep/keep.ico"
        },
        {
          "size": "48",
          "url": "https://ssl.gstatic.com/keep/icon_144.png"
        },
        {
          "size": "64",
          "url": "https://ssl.gstatic.com/keep/icon_144.png"
        },
        {
          "size": "96",
          "url": "https://ssl.gstatic.com/keep/icon_144.png"
        },
        {
          "size": "128",
          "url": "https://ssl.gstatic.com/keep/icon_144.png"
        },
        {
          "size": "144",
          "url": "https://ssl.gstatic.com/keep/icon_144.png"
        },
        {
          "size": "192",
          "url": "https://ssl.gstatic.com/keep/icon_192.png"
        },
        {
          "size": "256",
          "url": "https://ssl.gstatic.com/keep/icon_192.png"
        }
      ],
      "page_ordinal": "n"
    }
  },

Ok, I think I found the core issue after doing some more testing. The SSL certificate for the local addresses was not deployed correctly on devices B and C.

I was able to sync one app (from A) including the correct icon to device C after going to the app manually one time (on C) and consenting to the security warning.

Then I correctly deployed the certificate on device C and was able to sync another app (from a different address) (from A) with the right icon without ever having to visit the site on device C.

Is it intended behaviour to not sync the icon when there is something wrong with the site's certificate? If yes, I guess this doesn't need fixing and will just remain an issue for fringe cases such as local development apps or consumer NAS setups where users don't bother to install certificates.

That specific behaviour is not intentional. The way the sync works is that the URL of the icons are synced, not the data of the icon. Then when apps are synced the icons are downloaded. It sounds like the second device could not download the icons due to the missing SSL certificate.

Marking WontFix as that is the expected behavior with the current system. Please comment if you disagree or just want to discuss more. FWIW we have discussed syncing the icon data instead of the icon URL, but it isn't something that the sync system supports currently.

The decision is fine for me. I was just worried about corporate intranet applications, but usually the certificates should be deployed correctly in such environments.

As it likely affects only a small fraction of users (with missing/invalid certificates) changing the current sync system (syncing icon data) is not worth the effort.

As mentioned in  Issue #601646  I think it makes more sense to think about periodic icon updates in case there are new ones or higher resolution versions available. Both apps in the picture attached are manually added bookmark apps. I would need to regularly check if there is an updatedd icon for Google Docs available to ever get one with a high resolution.

Also this issue (with missing certificates) would be solved and the icon fetched/updated after the user visits the web app for the first time.

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