diff --git a/sdks/python/boxlite/errors.py b/sdks/python/boxlite/errors.py
index 482c7301a..55ac83803 100644
--- a/sdks/python/boxlite/errors.py
+++ b/sdks/python/boxlite/errors.py
@@ -7,6 +7,14 @@
 __all__ = ["BoxliteError", "ExecError", "TimeoutError", "ParseError"]
 
 
+def _exec_start_exit_code(stderr: str) -> int:
+    """Map command-start errors to shell-compatible exit codes."""
+    detail = stderr.lower()
+    if "no such file or directory" in detail:
+        return 127
+    return 126
+
+
 class BoxliteError(Exception):
     """Base exception for all boxlite errors."""
 
diff --git a/sdks/python/boxlite/simplebox.py b/sdks/python/boxlite/simplebox.py
index bc56cc638..be08cd35f 100644
--- a/sdks/python/boxlite/simplebox.py
+++ b/sdks/python/boxlite/simplebox.py
@@ -9,8 +9,19 @@
 from enum import IntEnum
 from typing import Optional, TYPE_CHECKING
 
+from .errors import ExecError, _exec_start_exit_code
 from .exec import ExecResult
 
+try:
+    from .boxlite import _ExecStartError
+except ImportError:
+
+    class _ExecStartError(RuntimeError):
+        """Import placeholder when the native extension is unavailable."""
+
+        pass
+
+
 if TYPE_CHECKING:
     from .boxlite import Boxlite
 
@@ -266,10 +277,18 @@ async def exec(
         # Convert env dict to list of tuples if provided
         env_list = list(env.items()) if env else None
 
+        command_display = " ".join([cmd, *args])
+
         # Execute via Rust (returns PyExecution)
-        execution = await self._box.exec(
-            cmd, arg_list, env_list, user=user, timeout_secs=timeout, cwd=cwd
-        )
+        try:
+            execution = await self._box.exec(
+                cmd, arg_list, env_list, user=user, timeout_secs=timeout, cwd=cwd
+            )
+        except _ExecStartError as e:
+            message = str(e)
+            raise ExecError(
+                command_display, _exec_start_exit_code(message), message
+            ) from e
 
         # Get streams from Rust execution
         try:
diff --git a/sdks/python/boxlite/sync_api/_simplebox.py b/sdks/python/boxlite/sync_api/_simplebox.py
index 6406e81af..274a9642e 100644
--- a/sdks/python/boxlite/sync_api/_simplebox.py
+++ b/sdks/python/boxlite/sync_api/_simplebox.py
@@ -9,8 +9,19 @@
 import logging
 from typing import TYPE_CHECKING, Dict, Optional
 
+from ..errors import ExecError, _exec_start_exit_code
 from ..exec import ExecResult
 
+try:
+    from ..boxlite import _ExecStartError
+except ImportError:
+
+    class _ExecStartError(RuntimeError):
+        """Import placeholder when the native extension is unavailable."""
+
+        pass
+
+
 if TYPE_CHECKING:
     from ._boxlite import SyncBoxlite
     from ._box import SyncBox
@@ -190,11 +201,18 @@ def exec(
 
         # Access the underlying async Box directly
         async_box = self._box._box
+        command_display = " ".join([cmd, *args])
 
         async def _exec_and_collect():
-            execution = await async_box.exec(
-                cmd, arg_list, env_list, user=user, timeout_secs=timeout, cwd=cwd
-            )
+            try:
+                execution = await async_box.exec(
+                    cmd, arg_list, env_list, user=user, timeout_secs=timeout, cwd=cwd
+                )
+            except _ExecStartError as e:
+                message = str(e)
+                raise ExecError(
+                    command_display, _exec_start_exit_code(message), message
+                ) from e
 
             stdout_lines = []
             stderr_lines = []
diff --git a/sdks/python/src/box_handle.rs b/sdks/python/src/box_handle.rs
index 3a49adddf..cafdd061c 100644
--- a/sdks/python/src/box_handle.rs
+++ b/sdks/python/src/box_handle.rs
@@ -6,7 +6,7 @@ use crate::metrics::PyBoxMetrics;
 use crate::network::PyNetworkHandle;
 use crate::snapshot_options::{PyCloneOptions, PyExportOptions};
 use crate::snapshots::PySnapshotHandle;
-use crate::util::map_err;
+use crate::util::{map_err, map_exec_start_err};
 use boxlite::{BoxCommand, CloneOptions, ExportOptions, LiteBox};
 use pyo3::prelude::*;
 
@@ -87,7 +87,7 @@ impl PyBox {
                 cmd = cmd.working_dir(cwd);
             }
 
-            let execution = handle.exec(cmd).await.map_err(map_err)?;
+            let execution = handle.exec(cmd).await.map_err(map_exec_start_err)?;
 
             Ok(PyExecution {
                 execution: Arc::new(execution),
diff --git a/sdks/python/src/lib.rs b/sdks/python/src/lib.rs
index 6ff730b17..5faa9937c 100644
--- a/sdks/python/src/lib.rs
+++ b/sdks/python/src/lib.rs
@@ -28,6 +28,7 @@ use crate::options::{
 use crate::runtime::PyBoxlite;
 use crate::snapshot_options::{PyCloneOptions, PyExportOptions, PySnapshotOptions};
 use crate::snapshots::{PySnapshotHandle, PySnapshotInfo};
+use crate::util::ExecStartError;
 use crate::volumes::{PyVolumeHandle, PyVolumeInfo};
 use pyo3::prelude::*;
 
@@ -71,6 +72,7 @@ fn boxlite_python(m: &Bound<'_, PyModule>) -> PyResult<()> {
     m.add_class::<PyApiKeyCredential>()?;
     m.add_class::<PyAccessToken>()?;
     m.add_class::<PySecret>()?;
+    m.add("_ExecStartError", m.py().get_type::<ExecStartError>())?;
 
     Ok(())
 }
diff --git a/sdks/python/src/util.rs b/sdks/python/src/util.rs
index ea544c5b5..753d0cff7 100644
--- a/sdks/python/src/util.rs
+++ b/sdks/python/src/util.rs
@@ -1,5 +1,27 @@
-use pyo3::{exceptions::PyRuntimeError, prelude::*};
+use boxlite::BoxliteError;
+use pyo3::{create_exception, exceptions::PyRuntimeError, prelude::*};
+
+create_exception!(boxlite_python, ExecStartError, PyRuntimeError);
+
+const EXEC_START_REASON: &str = "spawn_failed";
 
 pub(crate) fn map_err(err: impl std::fmt::Display) -> PyErr {
     PyRuntimeError::new_err(err.to_string())
 }
+
+pub(crate) fn map_exec_start_err(err: BoxliteError) -> PyErr {
+    if is_exec_start_failure(&err) {
+        ExecStartError::new_err(err.to_string())
+    } else {
+        map_err(err)
+    }
+}
+
+fn is_exec_start_failure(err: &BoxliteError) -> bool {
+    let BoxliteError::Internal(message) = err else {
+        return false;
+    };
+    message
+        .strip_prefix(EXEC_START_REASON)
+        .is_some_and(|detail| detail.starts_with(": "))
+}
diff --git a/sdks/python/tests/test_errors.py b/sdks/python/tests/test_errors.py
index fc7703c3d..316c88c65 100644
--- a/sdks/python/tests/test_errors.py
+++ b/sdks/python/tests/test_errors.py
@@ -5,7 +5,7 @@
 """
 
 import pytest
-from boxlite.errors import BoxliteError, ExecError, TimeoutError, ParseError
+from boxlite.errors import BoxliteError, ExecError, ParseError, TimeoutError
 
 
 class TestBoxliteError:
diff --git a/sdks/python/tests/test_simplebox.py b/sdks/python/tests/test_simplebox.py
index 3f6d9601c..8ac475fd1 100644
--- a/sdks/python/tests/test_simplebox.py
+++ b/sdks/python/tests/test_simplebox.py
@@ -16,3 +16,24 @@ async def test_simplebox_metrics(shared_runtime):
         metrics = await box.metrics()
         assert metrics is not None
         assert metrics.commands_executed_total >= 1
+
+
+async def test_simplebox_command_not_found_raises_exec_error(shared_runtime):
+    """Direct command start failures raise ExecError, not bare RuntimeError."""
+    async with boxlite.SimpleBox(image="alpine:latest", runtime=shared_runtime) as box:
+        with pytest.raises(boxlite.ExecError) as exc:
+            await box.exec("definitely-not-a-boxlite-command-xyz")
+        assert exc.value.exit_code == 127
+        stderr = exc.value.stderr.lower()
+        assert "failed to spawn" in stderr
+
+
+async def test_simplebox_unexecutable_command_raises_exit_code_126(shared_runtime):
+    async with boxlite.SimpleBox(image="alpine:latest", runtime=shared_runtime) as box:
+        await box.exec(
+            "sh", "-c", "printf '#!/bin/sh\\n' > /tmp/noexec && chmod 644 /tmp/noexec"
+        )
+        with pytest.raises(boxlite.ExecError) as exc:
+            await box.exec("/tmp/noexec")
+        assert exc.value.exit_code == 126
+        assert "permission denied" in exc.value.stderr.lower()
diff --git a/sdks/python/tests/test_sync_simplebox.py b/sdks/python/tests/test_sync_simplebox.py
index 928cfd031..6f7eaaa78 100644
--- a/sdks/python/tests/test_sync_simplebox.py
+++ b/sdks/python/tests/test_sync_simplebox.py
@@ -11,7 +11,7 @@
 
 # Try to import sync API - skip if greenlet not installed
 try:
-    from boxlite import SyncSimpleBox
+    from boxlite import ExecError, SyncSimpleBox
 
     SYNC_AVAILABLE = True
 except ImportError:
@@ -82,6 +82,25 @@ def test_metrics(self, shared_sync_runtime):
             assert metrics is not None
             assert metrics.commands_executed_total >= 1
 
+    def test_command_not_found_raises_exec_error(self, shared_sync_runtime):
+        """Direct command start failures raise ExecError, not bare RuntimeError."""
+        with SyncSimpleBox(image="alpine:latest", runtime=shared_sync_runtime) as box:
+            with pytest.raises(ExecError) as exc:
+                box.exec("definitely-not-a-boxlite-command-xyz")
+            assert exc.value.exit_code == 127
+
+    def test_unexecutable_command_raises_exit_code_126(self, shared_sync_runtime):
+        with SyncSimpleBox(image="alpine:latest", runtime=shared_sync_runtime) as box:
+            box.exec(
+                "sh",
+                "-c",
+                "printf '#!/bin/sh\\n' > /tmp/noexec && chmod 644 /tmp/noexec",
+            )
+            with pytest.raises(ExecError) as exc:
+                box.exec("/tmp/noexec")
+            assert exc.value.exit_code == 126
+            assert "permission" in exc.value.stderr.lower()
+
     def test_custom_working_dir(self, shared_sync_runtime):
         """Can set custom working directory."""
         with SyncSimpleBox(