diff --git a/internal/policy/engine.go b/internal/policy/engine.go
index 9a85073..0563d78 100644
--- a/internal/policy/engine.go
+++ b/internal/policy/engine.go
@@ -193,11 +193,15 @@ func matchPath(pattern, path string) bool {
 // Supports * as a wildcard for a single path segment.
 // Supports ** or trailing * for matching multiple segments.
 func MatchGlob(pattern, path string) bool {
-	// Trailing wildcard: "/tasks*" or "/tasks/*"
+	// Trailing wildcard: "/tasks*" or "/tasks/*" matches multiple segments
 	if strings.HasSuffix(pattern, "*") && !strings.HasSuffix(pattern, "**") {
 		prefix := strings.TrimSuffix(pattern, "*")
 		prefix = strings.TrimSuffix(prefix, "/")
-		return strings.HasPrefix(path, prefix)
+		if !strings.Contains(prefix, "*") {
+			return strings.HasPrefix(path, prefix)
+		}
+		// Mid-path wildcards present: promote trailing * to ** for segment matching
+		pattern = pattern[:len(pattern)-1] + "**"
 	}
 
 	patternParts := strings.Split(strings.Trim(pattern, "/"), "/")
diff --git a/internal/policy/engine_test.go b/internal/policy/engine_test.go
index 6e59a1c..3cde300 100644
--- a/internal/policy/engine_test.go
+++ b/internal/policy/engine_test.go
@@ -191,6 +191,31 @@ func TestEngine_GlobPatternDoubleWildcard(t *testing.T) {
 	}
 }
 
+func TestEngine_GlobTrailingWildcardWithMidPathWildcard(t *testing.T) {
+	rules := []config.Rule{
+		{Match: config.Match{Method: "POST", Path: "/client/v4/accounts/*/ai-search/*"}, Action: "allow"},
+		{Match: config.Match{Method: "*"}, Action: "deny"},
+	}
+	engine := New(rules)
+
+	tests := []struct {
+		path   string
+		expect Action
+	}{
+		{"/client/v4/accounts/abc123/ai-search/query", Allow},
+		{"/client/v4/accounts/abc123/ai-search/instances/kb/search", Allow},
+		{"/client/v4/accounts/abc123/other/stuff", Deny},
+		{"/client/v4/accounts/abc123/ai-search", Deny},
+	}
+
+	for _, tt := range tests {
+		decision := engine.Evaluate("POST", tt.path)
+		if decision.Action != tt.expect {
+			t.Errorf("POST %s: expected %v, got %v", tt.path, tt.expect, decision.Action)
+		}
+	}
+}
+
 func TestEngine_RateLimiting(t *testing.T) {
 	rules := []config.Rule{
 		{
diff --git a/internal/proxy/http.go b/internal/proxy/http.go
index aacc8e8..e9c3b40 100644
--- a/internal/proxy/http.go
+++ b/internal/proxy/http.go
@@ -266,7 +266,6 @@ func (p *Proxy) resolveUpstream(r *http.Request) (*url.URL, error) {
 // processSealedHeaders decrypts X-Wardgate-Sealed-* headers and sets the real
 // headers on the outgoing request. Only headers in the allowed whitelist are processed.
 func (p *Proxy) processSealedHeaders(req *http.Request, incoming http.Header) {
-	// Remove agent's Wardgate auth header before setting decrypted values
 	req.Header.Del("Authorization")
 
 	for name, values := range incoming {
@@ -279,19 +278,33 @@ func (p *Proxy) processSealedHeaders(req *http.Request, incoming http.Header) {
 			req.Header.Del(name)
 			continue
 		}
-		req.Header.Del(realHeader) // clear before Add loop so only decrypted values remain
+		req.Header.Del(realHeader)
 		for _, sealed := range values {
-			plaintext, err := p.sealer.Decrypt(sealed)
+			scheme, ciphertext := splitAuthScheme(sealed)
+			plaintext, err := p.sealer.Decrypt(ciphertext)
 			if err != nil {
 				log.Printf("failed to decrypt sealed header %q: %v", realHeader, err)
 				continue
 			}
-			req.Header.Add(realHeader, plaintext)
+			req.Header.Add(realHeader, scheme+plaintext)
 		}
 		req.Header.Del(name)
 	}
 }
 
+// splitAuthScheme strips a known HTTP auth scheme prefix (e.g. "Bearer ") from
+// a sealed header value so the remaining base64 ciphertext can be decrypted.
+// The prefix is returned separately so it can be re-added after decryption.
+// Valid base64 never contains spaces, so this never false-matches a pure sealed blob.
+func splitAuthScheme(value string) (scheme, ciphertext string) {
+	for _, prefix := range []string{"Bearer ", "Basic "} {
+		if strings.HasPrefix(value, prefix) {
+			return prefix, value[len(prefix):]
+		}
+	}
+	return "", value
+}
+
 // modifyResponse filters sensitive data from response bodies.
 func (p *Proxy) modifyResponse(resp *http.Response) error {
 	// Skip if no filter configured or filter is disabled
diff --git a/internal/proxy/http_test.go b/internal/proxy/http_test.go
index 71f5aa1..f841d37 100644
--- a/internal/proxy/http_test.go
+++ b/internal/proxy/http_test.go
@@ -1056,6 +1056,66 @@ func TestProxy_SealedMultipleValuesForSameHeader(t *testing.T) {
 	}
 }
 
+func TestSplitAuthScheme(t *testing.T) {
+	tests := []struct {
+		input      string
+		wantScheme string
+		wantRest   string
+	}{
+		{"Bearer abc123", "Bearer ", "abc123"},
+		{"Basic dXNlcjpwYXNz", "Basic ", "dXNlcjpwYXNz"},
+		{"abc123noprefix", "", "abc123noprefix"},
+		{"", "", ""},
+		{"bearer lowercase", "", "bearer lowercase"},
+	}
+	for _, tt := range tests {
+		scheme, rest := splitAuthScheme(tt.input)
+		if scheme != tt.wantScheme || rest != tt.wantRest {
+			t.Errorf("splitAuthScheme(%q) = (%q, %q), want (%q, %q)",
+				tt.input, scheme, rest, tt.wantScheme, tt.wantRest)
+		}
+	}
+}
+
+func TestProxy_SealedBearerPrefixStripped(t *testing.T) {
+	var receivedAuth string
+	upstream := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		receivedAuth = r.Header.Get("Authorization")
+		w.WriteHeader(http.StatusOK)
+	}))
+	defer upstream.Close()
+
+	sealer := newTestSealer(t)
+	// Seal just the API key (not "Bearer <key>") to match how the sandbox DO works
+	sealedKey, _ := sealer.Encrypt("sk-real-api-key-12345")
+
+	vault := &mockVault{creds: map[string]string{}}
+	endpoint := config.Endpoint{
+		Upstream: upstream.URL,
+		Auth:     config.AuthConfig{Sealed: true},
+	}
+	engine := policy.New([]config.Rule{{Match: config.Match{Method: "*"}, Action: "allow"}})
+
+	p := New(endpoint, vault, engine)
+	p.SetSealer(sealer)
+	p.SetAllowedSealHeaders(DefaultAllowedSealHeaders)
+
+	req := httptest.NewRequest("POST", "/responses", nil)
+	req.Header.Set("Authorization", "Bearer agent-jwt")
+	// SDK adds "Bearer " prefix to the sealed key, proxy renames the full value
+	req.Header.Set("X-Wardgate-Sealed-Authorization", "Bearer "+sealedKey)
+	rec := httptest.NewRecorder()
+
+	p.ServeHTTP(rec, req)
+
+	if rec.Code != http.StatusOK {
+		t.Fatalf("expected 200, got %d", rec.Code)
+	}
+	if receivedAuth != "Bearer sk-real-api-key-12345" {
+		t.Errorf("expected decrypted auth with Bearer prefix, got %q", receivedAuth)
+	}
+}
+
 func TestProxy_DynamicUpstreamAllowed(t *testing.T) {
 	var receivedHost string
 	upstream := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {