diff --git a/internal/env/env_test.go b/internal/env/env_test.go
new file mode 100644
index 00000000000..e23d91b8453
--- /dev/null
+++ b/internal/env/env_test.go
@@ -0,0 +1,42 @@
+package env
+
+import (
+	"github.com/stretchr/testify/require"
+	"os"
+	"testing"
+)
+
+func TestGetEnvBool(t *testing.T) {
+	envVarTestKey := "WAYPOINT_GET_ENV_BOOL_TEST"
+	require := require.New(t)
+
+	t.Run("Unset env var returns default", func (t *testing.T) {
+		require.True(GetEnvBool(envVarTestKey, true))
+		require.False(GetEnvBool(envVarTestKey, false))
+	})
+
+	t.Run("Empty env var returns default", func (t *testing.T) {
+		os.Setenv(envVarTestKey, "")
+		require.True(GetEnvBool(envVarTestKey, true))
+		require.False(GetEnvBool(envVarTestKey, false))
+	})
+
+	t.Run("Non-truthy env var returns true", func (t *testing.T) {
+		os.Setenv(envVarTestKey, "unparseable")
+		require.True(GetEnvBool(envVarTestKey, true))
+		require.False(GetEnvBool(envVarTestKey, false))
+	})
+
+	t.Run("true/false env vars return non-default", func (t *testing.T) {
+		os.Setenv(envVarTestKey, "true")
+		require.True(GetEnvBool(envVarTestKey, false))
+
+		os.Setenv(envVarTestKey, "false")
+		require.False(GetEnvBool(envVarTestKey, true))
+	})
+
+	t.Run("1 evaluates as true", func (t *testing.T) {
+		os.Setenv(envVarTestKey, "1")
+		require.True(GetEnvBool(envVarTestKey, false))
+	})
+}