diff --git a/eval/eval.go b/eval/eval.go
index e5ede0e..b37e25e 100644
--- a/eval/eval.go
+++ b/eval/eval.go
@@ -35,7 +35,7 @@ var exprEnvOptions = []expr.Option{
 	// Inject a custom isSorted function into the environment.
 	functions.IsSorted(),
 
-	// Provide a constant timestamp to the expression environment.
+  // Provide a constant timestamp to the expression environment.
 	expr.DisableBuiltin("now"),
 	expr.Function("now", func(...any) (any, error) {
 		return time.Date(2024, 2, 26, 0, 0, 0, 0, time.UTC).Format(time.RFC3339), nil
diff --git a/tests/regressions_test.go b/tests/regressions_test.go
new file mode 100644
index 0000000..f0cf726
--- /dev/null
+++ b/tests/regressions_test.go
@@ -0,0 +1,191 @@
+// Copyright 2024 Peter Olds <me@polds.dev>
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package tests
+
+import (
+	"encoding/json"
+	"fmt"
+	"os"
+	"strconv"
+	"testing"
+
+	"gopkg.in/yaml.v3"
+
+	"github.com/polds/expr-playground/eval"
+)
+
+// TestExamples serves as a regression test for the examples presented in the playground UI.
+// If any of the examples change, this test will fail, to help ensure the playground UI is
+// updated accordingly, and especially so we don't accidentally push a broken sample.
+func TestExamples(t *testing.T) {
+	examples := setup(t)
+
+	// lookup should exactly match the "name" field in the examples.yaml file.
+	tests := []struct {
+		lookup  string
+		want    string
+		wantErr bool
+	}{
+		{
+			lookup: "default",
+			want:   "true",
+		},
+		{
+			lookup: "Check image registry",
+			want:   "true",
+		},
+		{
+			lookup: "Disallow HostPorts",
+			want:   "false",
+		},
+		{
+			lookup: "Require non-root containers",
+			want:   "false",
+		},
+		{
+			lookup: "Drop ALL capabilities",
+			want:   "true",
+		},
+		{
+			lookup: "Semantic version check for image tags (Regex)",
+			want:   "false",
+		},
+		{
+			lookup:  "URLs",
+			wantErr: true,
+		},
+		{
+			lookup: "Check JWT custom claims",
+			want:   "true",
+		},
+		{
+			lookup: "Optional",
+			want:   "fallback",
+		},
+		{
+			lookup: "Duration and timestamp",
+			want:   "true",
+		},
+		{
+			lookup:  "Quantity",
+			wantErr: true,
+		},
+		{
+			lookup: "Access Log Filtering",
+			want:   "true",
+		},
+		{
+			lookup: "Custom Metrics",
+			want:   "echo",
+		},
+		{
+			lookup:  "Blank",
+			wantErr: true,
+		},
+	}
+	for _, tc := range tests {
+		t.Run(tc.lookup, func(t *testing.T) {
+			var exp Example
+			for _, e := range examples {
+				if e.Name == tc.lookup {
+					exp = e
+					break
+				}
+			}
+			if exp.Name == "" {
+				t.Fatalf("failed to find example %q", tc.lookup)
+			}
+
+			got, err := eval.Eval(exp.Expr, marshal(t, exp.Data))
+			if (err != nil) != tc.wantErr {
+				t.Errorf("Eval() got error %v, expected error %v", err, tc.wantErr)
+			}
+			if tc.wantErr {
+				return
+			}
+
+			var obj map[string]AlwaysString
+			if err := json.Unmarshal([]byte(got), &obj); err != nil {
+				t.Fatalf("failed to unmarshal response: %v", err)
+			}
+			if s := obj["result"].Value; s != tc.want {
+				t.Errorf("Eval() got %q, expected %q", s, tc.want)
+			}
+		})
+	}
+	// Ensure these tests are updated when the examples are updated.
+	// Not a perfect solution, but it's better than nothing.
+	if len(examples) != len(tests) {
+		t.Errorf("Regression test counts got %d, expected %d", len(tests), len(examples))
+	}
+}
+
+type Example struct {
+	Name string `yaml:"name"`
+	Expr string `yaml:"expr"`
+	Data string `yaml:"data"`
+}
+
+func setup(t *testing.T) []Example {
+	t.Helper()
+
+	out, err := os.ReadFile("../examples.yaml")
+	if err != nil {
+		t.Fatalf("failed to read examples.yaml: %v", err)
+	}
+	var examples struct {
+		Examples []Example `yaml:"examples"`
+	}
+	if err := yaml.Unmarshal(out, &examples); err != nil {
+		t.Fatalf("failed to unmarshal examples.yaml: %v", err)
+	}
+	return examples.Examples
+}
+
+// Attempt to get the data into either yaml or json format.
+func marshal(t *testing.T, s string) map[string]any {
+	t.Helper()
+
+	var v map[string]any
+	if yamlErr := yaml.Unmarshal([]byte(s), &v); yamlErr != nil {
+		if err := json.Unmarshal([]byte(s), &v); err != nil {
+			t.Errorf("failed to unmarshal %q as yaml: %v", s, yamlErr)
+			t.Fatalf("failed to unmarshal %q as json: %v", s, err)
+		}
+	}
+	return v
+}
+
+// AlwaysString attempts to unmarshal the value as a string.
+type AlwaysString struct {
+	Value string
+}
+
+func (c *AlwaysString) UnmarshalJSON(b []byte) error {
+	var raw any
+	if err := json.Unmarshal(b, &raw); err != nil {
+		return err
+	}
+
+	switch v := raw.(type) {
+	case bool:
+		c.Value = strconv.FormatBool(v)
+	case string:
+		c.Value = v
+	default:
+		return fmt.Errorf("unsupported type %T", v)
+	}
+	return nil
+}