diff --git a/.gitignore b/.gitignore
index 335b3214..2e9ad775 100644
--- a/.gitignore
+++ b/.gitignore
@@ -62,5 +62,6 @@ docs/_build/
 # OS specific
 .DS_Store
 Thumbs.db
+default.profraw
 
 tests/test_workspace
diff --git a/packages/cli/src/pywrangler/cli.py b/packages/cli/src/pywrangler/cli.py
index 890e8b28..046f70d7 100644
--- a/packages/cli/src/pywrangler/cli.py
+++ b/packages/cli/src/pywrangler/cli.py
@@ -8,6 +8,7 @@
 import click
 
 from .sync import sync
+from .unsupported_flags import find_unsupported_flag
 from .utils import (
     WRANGLER_COMMAND,
     WRANGLER_CREATE_COMMAND,
@@ -68,6 +69,11 @@ def get_command(self, ctx: click.Context, cmd_name: str) -> click.Command:
             except ValueError:
                 remaining_args = []
 
+            unsupported = find_unsupported_flag(cmd_name, remaining_args)
+            if unsupported is not None:
+                logger.error(unsupported.error_message())
+                sys.exit(1)
+
             if cmd_name in {"dev", "publish", "deploy", "versions", "preview"}:
                 sync(force=False)
 
diff --git a/packages/cli/src/pywrangler/unsupported_flags.py b/packages/cli/src/pywrangler/unsupported_flags.py
new file mode 100644
index 00000000..028c96fc
--- /dev/null
+++ b/packages/cli/src/pywrangler/unsupported_flags.py
@@ -0,0 +1,77 @@
+from collections.abc import Sequence
+from dataclasses import dataclass
+
+
+@dataclass(frozen=True)
+class UnsupportedFlag:
+    """A wrangler flag that pywrangler rejects before proxying."""
+
+    command: str
+    names: tuple[str, ...]
+    hint: str
+
+    def matches(self, cmd_name: str, args: Sequence[str]) -> bool:
+        if cmd_name != self.command:
+            return False
+        flag_args = _flag_args(args)
+        return any(
+            self._is_enabled(arg, flag_args[i + 1] if i + 1 < len(flag_args) else None)
+            for i, arg in enumerate(flag_args)
+        )
+
+    def _is_enabled(self, arg: str, next_arg: str | None) -> bool:
+        # Enabled by `--flag/-f`, unless followed by a separate `false` value
+        if arg in self.names:
+            return next_arg != "false"
+        # With `--flag=value`, enables the flag only for a literal `true`
+        # instestingly, wrangler ignores all other values other than `true/false`,
+        # so things like --flag=1 is the same as --flag=False
+        name, sep, value = arg.partition("=")
+        return bool(sep) and name in self.names and value == "true"
+
+    def error_message(self) -> str:
+        return (
+            f"`pywrangler {self.command} {self.names[0]}` is not supported "
+            f"for Python Workers.\n{self.hint}"
+        )
+
+
+UNSUPPORTED_FLAGS: tuple[UnsupportedFlag, ...] = (
+    UnsupportedFlag(
+        command="dev",
+        names=("--remote", "-r"),
+        hint=(
+            "Please use remote bindings instead.\n"
+            "See https://developers.cloudflare.com/workers/development-testing/#remote-bindings"
+        ),
+    ),
+)
+
+
+def find_unsupported_flag(
+    cmd_name: str,
+    args: Sequence[str],
+    registry: Sequence[UnsupportedFlag] = UNSUPPORTED_FLAGS,
+) -> UnsupportedFlag | None:
+    """
+    Find an unsupported flag in the given command and arguments.
+
+    Parameters
+    ----------
+    cmd_name:
+        The command name to check.
+    args:
+        The arguments to check.
+    registry:
+        The registry of unsupported flags to check against.
+        (For testing purposes. Normally not needed.)
+
+    Returns
+    -------
+        The unsupported flag if found, otherwise None.
+    """
+    return next((flag for flag in registry if flag.matches(cmd_name, args)), None)
+
+
+def _flag_args(args: Sequence[str]) -> Sequence[str]:
+    return args[: args.index("--")] if "--" in args else args
diff --git a/packages/cli/tests/test_cli.py b/packages/cli/tests/test_cli.py
index 71c578fb..2bb62986 100644
--- a/packages/cli/tests/test_cli.py
+++ b/packages/cli/tests/test_cli.py
@@ -690,6 +690,60 @@ def test_proxy_auto_sync_commands(
     mock_proxy_to_wrangler.assert_called_once_with("dev", ["--local"])
 
 
+@pytest.mark.parametrize(
+    "remote_args",
+    [
+        ["--remote"],
+        ["-r"],
+        ["--port", "8787", "--remote"],
+        ["--remote=true"],
+        ["--remote", "true"],
+    ],
+)
+@patch("pywrangler.utils.check_wrangler_version")
+@patch("pywrangler.cli._proxy_to_wrangler")
+@patch("pywrangler.cli.sync")
+def test_dev_remote_is_rejected(
+    mock_sync_command,
+    mock_proxy_to_wrangler,
+    mock_check_wrangler_version,
+    remote_args,
+    caplog,
+):
+    with patch("sys.argv", ["pywrangler", "dev", *remote_args]):
+        result = CliRunner().invoke(app, ["dev", *remote_args])
+
+    assert result.exit_code == 1
+    assert "remote bindings" in caplog.text
+    mock_sync_command.assert_not_called()
+    mock_proxy_to_wrangler.assert_not_called()
+
+
+@pytest.mark.parametrize(
+    "args", [["--remote", "false"], ["-r", "false"], ["--remote=false"]]
+)
+@patch("pywrangler.utils.check_wrangler_version")
+@patch("pywrangler.cli._proxy_to_wrangler")
+@patch("pywrangler.cli.sync")
+def test_dev_remote_disabled_is_proxied(
+    mock_sync_command, mock_proxy_to_wrangler, mock_check_wrangler_version, args
+):
+    with patch("sys.argv", ["pywrangler", "dev", *args]):
+        result = CliRunner().invoke(app, ["dev", *args])
+
+    assert result.exit_code == 0
+    mock_proxy_to_wrangler.assert_called_once_with("dev", args)
+
+
+@patch("pywrangler.cli._proxy_to_wrangler")
+@patch("sys.argv", ["pywrangler", "d1", "execute", "db", "--remote"])
+def test_remote_flag_allowed_for_non_dev_commands(mock_proxy_to_wrangler):
+    result = CliRunner().invoke(app, ["d1", "execute", "db", "--remote"])
+
+    assert result.exit_code == 0
+    mock_proxy_to_wrangler.assert_called_once_with("d1", ["execute", "db", "--remote"])
+
+
 @patch("pywrangler.cli.subprocess.run")
 def test_proxy_to_wrangler_handles_subprocess_error(mock_subprocess_run):
     """Test that subprocess errors are handled gracefully."""
diff --git a/packages/cli/tests/test_unsupported_flags.py b/packages/cli/tests/test_unsupported_flags.py
new file mode 100644
index 00000000..028bcfd6
--- /dev/null
+++ b/packages/cli/tests/test_unsupported_flags.py
@@ -0,0 +1,70 @@
+import pytest
+
+from pywrangler.unsupported_flags import (
+    UNSUPPORTED_FLAGS,
+    UnsupportedFlag,
+    find_unsupported_flag,
+)
+
+FLAG = UnsupportedFlag(command="dev", names=("--foo", "-f"), hint="Do X instead.")
+REGISTRY = (FLAG,)
+
+
+@pytest.mark.parametrize(
+    "args",
+    [
+        ["--foo"],
+        ["-f"],
+        ["--port", "8787", "--foo"],
+        ["--foo=true"],
+        ["-f=true"],
+        ["--foo", "true"],
+        ["--foo", "--port", "8787"],
+    ],
+)
+def test_enabled_flag_is_found(args):
+    assert find_unsupported_flag("dev", args, REGISTRY) is FLAG
+
+
+@pytest.mark.parametrize(
+    "args",
+    [
+        [],
+        ["--foobar"],
+        ["--foo=false"],
+        ["--foo=0"],
+        ["--foo=No"],
+        ["--foo=1"],
+        ["--foo=yes"],
+        ["--foo=TRUE"],
+        ["--foo="],
+        ["-f=0"],
+        ["--foo", "false"],
+        ["-f", "false"],
+        ["--foo", "false", "--port", "8787"],
+        ["--", "--foo"],
+    ],
+)
+def test_disabled_or_absent_flag_is_ignored(args):
+    assert find_unsupported_flag("dev", args, REGISTRY) is None
+
+
+def test_flag_is_scoped_to_its_command():
+    assert find_unsupported_flag("deploy", ["--foo"], REGISTRY) is None
+
+
+def test_error_message():
+    assert FLAG.error_message() == (
+        "`pywrangler dev --foo` is not supported for Python Workers.\nDo X instead."
+    )
+
+
+@pytest.mark.parametrize("args", [["--remote"], ["-r"], ["--remote=true"]])
+def test_default_registry_rejects_dev_remote(args):
+    flag = find_unsupported_flag("dev", args, UNSUPPORTED_FLAGS)
+    assert flag is not None
+    assert "remote bindings" in flag.error_message()
+
+
+def test_default_registry_allows_remote_for_other_commands():
+    assert find_unsupported_flag("d1", ["execute", "db", "--remote"]) is None