Yes — this is a known-but-obscure ChromeOS + Google Admin quirk, and you’re thinking in the right direction. The fact that it only fails on managed Chromebooks and only when typed directly is the key clue.

Below are the most common causes I’ve seen specifically produce this behavior, in roughly the order I’d check them.

Why Google Search works but typing the URL doesn’t

When you click a Google search result, Chrome does not navigate the same way as when you type a URL:

• Google Search links often:

  • Rewrite the URL (adds/removes www)

  • Force https

  • Bypass certain navigation policies

  • Pass through a Google redirect (https://www.google.com/url?...)

• Direct typing triggers Chrome navigation enforcement policies more strictly

So this is almost always a Chrome policy, not DNS or networking.

High-probability causes on Managed Chromebooks

1. URLBlocklist / URLAllowlist mismatch

Most common cause

If you have any URL blocking configured:

• Chrome evaluates typed URLs more strictly

• Google search clicks may still work if the resolved destination differs slightly

Things to check carefully:

• http://example.com vs https://example.com

• example.com vs www.example.com

• Subdomains (*.example.com)

🔍 Fix
In Google Admin → Devices → Chrome → Settings → Users & browsers:

Add explicit allow rules like:

https://example.com/*
https://www.example.com/*
http://example.com/*

Even if you think you already allowed it — add it again explicitly.

2. HTTPS-Only / Force HTTPS policy

If the site:

• Redirects oddly

• Has partial HTTPS support

• Uses legacy TLS

Typed navigation:

• Tries HTTPS first

• Fails hard

Google search:

• May redirect through a working endpoint

🔍 Check:

• Admin → Chrome → Security → Always use secure connections

• Chrome setting: chrome://policy

If this is on, try temporarily disabling it to test.

3. Certificate inspection / SSL decryption

Very common in school environments.

If:

• SSL inspection is enabled

• The site has a nonstandard cert chain

• Or uses SNI weirdness

Typed navigation fails
Google search → works (because Google proxying masks the cert)

🔍 Check:

• Admin → Networks → Certificate Authority

• Any filtering appliance (Lightspeed, GoGuardian, Securly, etc.)

Try:

• Temporarily bypassing SSL inspection for that domain

4. Proxy or PAC file behavior

Typed URLs and redirected URLs are sometimes routed differently.

Especially if you use:

• Explicit proxy

• PAC file

• Content filter

🔍 Check:

• Admin → Chrome → Network → Proxy settings

• Whether DIRECT vs PROXY rules differ by URL format

5. Safe Browsing / Content filtering classification

Even if the site isn’t blocked outright:

• Typed navigation may be blocked

• Search-click navigation allowed

🔍 Check:

• Safe Browsing level

• Content category blocks

• Admin → Chrome → Safety

6. Extensions forced by policy

Extensions can intercept navigation events.

Even if the extension is “passive”:

• Typed URLs trigger inspection

• Redirected URLs sometimes do not

🔍 Test:

• Temporarily disable all force-installed extensions

• Especially filtering, monitoring, or security extensions

Fastest way to pinpoint it

On the affected Chromebook:

1. Go to:

chrome://policy

2. Search for:

   • URLBlocklist

   • URLAllowlist

   • ProxyMode

   • HttpsOnlyMode

   • SafeBrowsing

3. Click “Reload policies”

4. Retest

If you want to go deeper:

chrome://net-export

and capture a failing vs working attempt.

TL;DR (what usually fixes it)

✅ Add explicit HTTPS + HTTP allow rules for the domain
✅ Check HTTPS-only enforcement
✅ Exclude the domain from SSL inspection / content filtering

If you want, tell me:

• Whether you’re using GoGuardian / Lightspeed / Securly / etc.

• Whether URL filtering is device- or user-based

I can point you to the exact toggle that usually causes this.