diff --git a/pkg/tools/shell.go b/pkg/tools/shell.go
index d13d8f9ce..f1ffbf872 100644
--- a/pkg/tools/shell.go
+++ b/pkg/tools/shell.go
@@ -419,21 +419,14 @@ func hasHTTPURLPrefix(command string, start int) bool {
 }
 
 func findHTTPURLEnd(command string, start int, quote byte) int {
-	if quote != 0 {
-		for i := start; i < len(command); i++ {
-			if quote == '"' && command[i] == '\\' && i+1 < len(command) {
-				i++
-				continue
-			}
-			if command[i] == quote {
-				return i
-			}
-		}
-		return len(command)
-	}
-
 	for i := start; i < len(command); i++ {
-		if strings.ContainsRune(" \t\r\n", rune(command[i])) || isShellURLDelimiter(command[i]) {
+		if quote != 0 && (command[i] == quote || command[i] == '\'' || command[i] == '"') {
+			return i
+		}
+		if quote == 0 && (strings.ContainsRune(" \t\r\n", rune(command[i])) || isShellURLDelimiter(command[i])) {
+			return i
+		}
+		if !isHTTPURLChar(command[i]) {
 			return i
 		}
 	}
@@ -441,6 +434,24 @@ func findHTTPURLEnd(command string, start int, quote byte) int {
 	return len(command)
 }
 
+func isHTTPURLChar(ch byte) bool {
+	switch {
+	case ch >= 'a' && ch <= 'z':
+		return true
+	case ch >= 'A' && ch <= 'Z':
+		return true
+	case ch >= '0' && ch <= '9':
+		return true
+	}
+
+	switch ch {
+	case ':', '/', '?', '#', '[', ']', '@', '!', '$', '&', '*', '+', ',', ';', '=', '%', '-', '.', '_', '~':
+		return true
+	default:
+		return false
+	}
+}
+
 func isShellURLDelimiter(ch byte) bool {
 	switch ch {
 	case ';', '|', '&', '<', '>', '(', ')', '`':
diff --git a/pkg/tools/shell_test.go b/pkg/tools/shell_test.go
index 0002b02ab..20fe6c53f 100644
--- a/pkg/tools/shell_test.go
+++ b/pkg/tools/shell_test.go
@@ -359,6 +359,28 @@ func TestShellTool_RestrictToWorkspace_URLDoesNotBypassPathChecks(t *testing.T)
 	}
 }
 
+// TestShellTool_RestrictToWorkspace_URLDoesNotMaskQuotedPaths verifies that a
+// URL inside a quoted argument does not hide a later absolute path in the same argument.
+func TestShellTool_RestrictToWorkspace_URLDoesNotMaskQuotedPaths(t *testing.T) {
+	tmpDir := t.TempDir()
+	tool, err := NewExecTool(tmpDir, true)
+	if err != nil {
+		t.Fatalf("unable to configure exec tool: %s", err)
+	}
+
+	commands := []string{
+		`python3 -c "print('https://x,' + open('/etc/passwd').read())"`,
+		`python3 -c "print('https://x,'+open('/etc/passwd').read())"`,
+	}
+
+	for _, cmd := range commands {
+		result := tool.Execute(context.Background(), map[string]any{"command": cmd})
+		if !result.IsError || !strings.Contains(result.ForLLM, "blocked") {
+			t.Fatalf("expected quoted path access to stay blocked, command=%q output=%s", cmd, result.ForLLM)
+		}
+	}
+}
+
 // TestShellTool_DevNullAllowed verifies that /dev/null redirections are not blocked (issue #964).
 func TestShellTool_DevNullAllowed(t *testing.T) {
 	tmpDir := t.TempDir()