diff --git a/src/main.rs b/src/main.rs
index aaf5840..fe84332 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -4,9 +4,9 @@ mod config;
 mod output;
 mod shell;
 
-use std::process::ExitCode;
+use std::{ffi::OsStr, process::ExitCode};
 
-use clap::{Parser, Subcommand};
+use clap::{Parser, Subcommand, error::ErrorKind};
 use output::OutputFormat;
 
 #[derive(Parser)]
@@ -68,7 +68,31 @@ enum Commands {
 
 #[tokio::main]
 async fn main() -> ExitCode {
-    let cli = Cli::parse();
+    let args: Vec<_> = std::env::args_os().collect();
+    let requested_output = requested_output_format(&args[1..]);
+    let cli = match Cli::try_parse_from(args) {
+        Ok(cli) => cli,
+        Err(error) => {
+            if matches!(
+                error.kind(),
+                ErrorKind::DisplayHelp | ErrorKind::DisplayVersion
+            ) {
+                error.exit();
+            }
+
+            if matches!(requested_output, OutputFormat::Json) {
+                println!(
+                    "{}",
+                    serde_json::json!({
+                        "error": error.to_string(),
+                    })
+                );
+                return ExitCode::from(u8::try_from(error.exit_code()).unwrap_or(1));
+            }
+
+            error.exit();
+        }
+    };
     let output = cli.output;
 
     if let Err(e) = run(cli).await {
@@ -79,6 +103,40 @@ async fn main() -> ExitCode {
     ExitCode::SUCCESS
 }
 
+fn requested_output_format(args: &[impl AsRef<OsStr>]) -> OutputFormat {
+    let mut requested = OutputFormat::Table;
+    let mut args = args.iter();
+
+    while let Some(arg) = args.next() {
+        let arg = arg.as_ref();
+        if arg == "--" {
+            break;
+        }
+
+        if arg == "--output" || arg == "-o" {
+            if args.next().is_some_and(|value| value.as_ref() == "json") {
+                requested = OutputFormat::Json;
+            }
+            continue;
+        }
+
+        let Some(arg) = arg.to_str() else {
+            continue;
+        };
+        if arg
+            .strip_prefix("--output=")
+            .is_some_and(|value| value == "json")
+            || arg
+                .strip_prefix("-o")
+                .is_some_and(|value| !value.is_empty() && value == "json")
+        {
+            requested = OutputFormat::Json;
+        }
+    }
+
+    requested
+}
+
 #[allow(clippy::too_many_lines)]
 pub(crate) async fn run(cli: Cli) -> anyhow::Result<()> {
     // Lazy-init so we only pay for the client we actually use.
diff --git a/tests/cli_integration.rs b/tests/cli_integration.rs
index 41d3d11..eb861db 100644
--- a/tests/cli_integration.rs
+++ b/tests/cli_integration.rs
@@ -91,11 +91,67 @@ fn no_args_shows_usage() {
         .stderr(predicate::str::contains("Usage"));
 }
 
+fn assert_json_parse_error(args: &[&str]) {
+    let output = polymarket().args(args).output().unwrap();
+
+    assert_eq!(output.status.code(), Some(2));
+    assert!(
+        output.stderr.is_empty(),
+        "stderr should be empty in JSON mode: {}",
+        String::from_utf8_lossy(&output.stderr)
+    );
+
+    let stdout = String::from_utf8_lossy(&output.stdout);
+    let parsed: serde_json::Value = serde_json::from_str(stdout.trim())
+        .unwrap_or_else(|e| panic!("stdout not valid JSON: {e}\nstdout: {stdout}"));
+    assert!(
+        parsed
+            .get("error")
+            .is_some_and(serde_json::Value::is_string),
+        "missing string 'error' key: {parsed}"
+    );
+}
+
 #[test]
 fn unknown_command_fails() {
     polymarket().arg("nonexistent").assert().failure();
 }
 
+#[test]
+fn json_mode_formats_unknown_command_parse_error() {
+    assert_json_parse_error(&["--output", "json", "nonexistent"]);
+}
+
+#[test]
+fn json_mode_is_detected_after_invalid_command() {
+    assert_json_parse_error(&["nonexistent", "--output=json"]);
+}
+
+#[test]
+fn json_short_form_formats_validation_error() {
+    assert_json_parse_error(&["markets", "get", "-ojson"]);
+}
+
+#[test]
+fn table_mode_parse_error_keeps_clap_output() {
+    polymarket()
+        .arg("nonexistent")
+        .assert()
+        .code(2)
+        .stdout(predicate::str::is_empty())
+        .stderr(predicate::str::starts_with("error:").and(predicate::str::contains("Usage:")));
+}
+
+#[test]
+fn json_flag_does_not_change_help_semantics() {
+    polymarket()
+        .args(["--output", "json", "--help"])
+        .assert()
+        .success()
+        .stdout(predicate::str::contains("Usage:"))
+        .stderr(predicate::str::is_empty());
+}
+
 #[test]
 fn invalid_output_format_rejected() {
     polymarket()