diff --git a/Sources/Brave/Frontend/Browser/BrowserViewController/BVC+WKNavigationDelegate.swift b/Sources/Brave/Frontend/Browser/BrowserViewController/BVC+WKNavigationDelegate.swift
index e31ce286f382..fdd5c182ea65 100644
--- a/Sources/Brave/Frontend/Browser/BrowserViewController/BVC+WKNavigationDelegate.swift
+++ b/Sources/Brave/Frontend/Browser/BrowserViewController/BVC+WKNavigationDelegate.swift
@@ -67,11 +67,14 @@ extension BrowserViewController: WKNavigationDelegate {
     // check if web view is loading a different origin than the one currently loaded
     if let selectedTab = tabManager.selectedTab,
        selectedTab.url?.origin != webView.url?.origin {
-      // reset secure content state to unknown until page can be evaluated
-      if let url = webView.url, !InternalURL.isValid(url: url) {
-        selectedTab.secureContentState = .unknown
-        updateToolbarSecureContentState(.unknown)
+      if let url = webView.url {
+        if !InternalURL.isValid(url: url) {
+          // reset secure content state to unknown until page can be evaluated
+          selectedTab.secureContentState = .unknown
+          updateToolbarSecureContentState(.unknown)
+        }
       }
+      
       // new site has a different origin, hide wallet icon.
       tabManager.selectedTab?.isWalletIconVisible = false
       // new site, reset connected addresses
@@ -672,9 +675,19 @@ extension BrowserViewController: WKNavigationDelegate {
 
   public func webView(_ webView: WKWebView, didCommit navigation: WKNavigation!) {
     guard let tab = tab(for: webView) else { return }
+
     // Set the committed url which will also set tab.url
     tab.committedURL = webView.url
     
+    // Server Trust and URL is also updated in didCommit
+    // However, WebKit does NOT trigger the `serverTrust` observer when the URL changes, but the trust has not.
+    // WebKit also does NOT trigger the `serverTrust` observer when the page is actually insecure (non-https).
+    // So manually trigger it with the current trust.
+    observeValue(forKeyPath: KVOConstants.serverTrust.keyPath,
+                 of: webView,
+                 change: [.newKey: webView.serverTrust as Any, .kindKey: 1],
+                 context: nil)
+    
     // Need to evaluate Night mode script injection after url is set inside the Tab
     tab.nightMode = Preferences.General.nightModeEnabled.value
     tab.clearSolanaConnectedAccounts()
diff --git a/Sources/Brave/Frontend/Browser/BrowserViewController/BrowserViewController.swift b/Sources/Brave/Frontend/Browser/BrowserViewController/BrowserViewController.swift
index 89f1f7ee5ec8..20fab8f34f0f 100644
--- a/Sources/Brave/Frontend/Browser/BrowserViewController/BrowserViewController.swift
+++ b/Sources/Brave/Frontend/Browser/BrowserViewController/BrowserViewController.swift
@@ -1817,9 +1817,33 @@ public class BrowserViewController: UIViewController {
         if let url = tab.webView?.url, url.isReaderModeURL {
           break
         }
+        
         tab.secureContentState = .mixedContent
       }
-
+      
+      if let url = tab.webView?.url,
+         InternalURL.isValid(url: url),
+         let internalUrl = InternalURL(url) {
+        
+        if internalUrl.isErrorPage {
+          if ErrorPageHelper.certificateError(for: url) != 0 {
+            // Cert validation takes precedence over all other errors
+            tab.secureContentState = .invalidCert
+          } else if NetworkErrorPageHandler.isNetworkError(errorCode: ErrorPageHelper.errorCode(for: url)) {
+            // Network error takes precedence over missing cert
+            // Because we cannot determine if a cert is missing yet, if we cannot connect to the server
+            // Our network interstitial page shows
+            tab.secureContentState = .localhost
+          } else {
+            // Since it's not a cert error explicitly, and it's not a network error, and the cert is missing (no serverTrust),
+            // then we display .missingSSL
+            tab.secureContentState = .missingSSL
+          }
+        } else if url.isReaderModeURL || InternalURL.isValid(url: url) {
+          tab.secureContentState = .localhost
+        }
+      }
+      
       if tabManager.selectedTab === tab {
         updateToolbarSecureContentState(tab.secureContentState)
       }
@@ -1848,10 +1872,19 @@ public class BrowserViewController: UIViewController {
             internalUrl.isErrorPage {
 
             if ErrorPageHelper.certificateError(for: url) != 0 {
+              // Cert validation takes precedence over all other errors
               tab.secureContentState = .invalidCert
+            } else if NetworkErrorPageHandler.isNetworkError(errorCode: ErrorPageHelper.errorCode(for: url)) {
+              // Network error takes precedence over missing cert
+              // Because we cannot determine if a cert is missing yet, if we cannot connect to the server
+              // Our network interstitial page shows
+              tab.secureContentState = .localhost
             } else {
+              // Since it's not a cert error explicitly, and it's not a network error, and the cert is missing (no serverTrust),
+              // then we display .missingSSL
               tab.secureContentState = .missingSSL
             }
+            
             if tabManager.selectedTab === tab {
               updateToolbarSecureContentState(tab.secureContentState)
             }
diff --git a/Sources/Brave/Frontend/Browser/Helpers/ErrorPageHelper.swift b/Sources/Brave/Frontend/Browser/Helpers/ErrorPageHelper.swift
index e255e887d373..5a01cb4ddc1a 100644
--- a/Sources/Brave/Frontend/Browser/Helpers/ErrorPageHelper.swift
+++ b/Sources/Brave/Frontend/Browser/Helpers/ErrorPageHelper.swift
@@ -135,18 +135,32 @@ class ErrorPageHelper {
 }
 
 extension ErrorPageHelper {
-  static func certificateError(for url: URL) -> Int {
+  static func errorCode(for url: URL) -> Int {
+    // ErrorCode is zero if there's no error.
+    // Non-Zero (negative or positive) when there is an error
+    
     if InternalURL.isValid(url: url),
       let internalUrl = InternalURL(url),
-      internalUrl.isErrorPage {
-
+       internalUrl.isErrorPage {
+      
       let query = url.getQuery()
       guard let code = query["code"],
-        let errCode = Int(code)
+            let errCode = Int(code)
       else {
         return 0
       }
-
+      
+      return errCode
+    }
+    return 0
+  }
+  
+  static func certificateError(for url: URL) -> Int {
+    let errCode = errorCode(for: url)
+    
+    // ErrorCode is zero if there's no error.
+    // Non-Zero (negative or positive) when there is an error
+    if errCode != 0 {
       if let code = CFNetworkErrors(rawValue: Int32(errCode)),
         CertificateErrorPageHandler.CFNetworkErrorsCertErrors.contains(code) {
         return errCode
diff --git a/Sources/Brave/Frontend/Browser/Interstitial Pages/NetworkErrorPageHandler.swift b/Sources/Brave/Frontend/Browser/Interstitial Pages/NetworkErrorPageHandler.swift
index c3de4df5364c..43cd73c9a556 100644
--- a/Sources/Brave/Frontend/Browser/Interstitial Pages/NetworkErrorPageHandler.swift	
+++ b/Sources/Brave/Frontend/Browser/Interstitial Pages/NetworkErrorPageHandler.swift	
@@ -8,6 +8,14 @@ import Shared
 import BraveShared
 
 class NetworkErrorPageHandler: InterstitialPageHandler {
+  static func isNetworkError(errorCode: Int) -> Bool {
+    if let code = CFNetworkErrors(rawValue: Int32(errorCode)) {
+      return code == .cfurlErrorNotConnectedToInternet
+    }
+
+    return errorCode == NSURLErrorNotConnectedToInternet
+  }
+  
   func canHandle(error: NSError) -> Bool {
     // Handle CFNetwork Error
     if error.domain == kCFErrorDomainCFNetwork as String,