diff --git a/expectation.not.go b/expectation.not.go
new file mode 100644
index 00000000..c33a3b47
--- /dev/null
+++ b/expectation.not.go
@@ -0,0 +1,67 @@
+package testkit
+
+import (
+	"fmt"
+
+	"github.com/dogmatiq/testkit/fact"
+)
+
+// Not is an expectation that passes only if the given expectation fails.
+func Not(expectation Expectation) Expectation {
+	return &notExpectation{
+		caption:     fmt.Sprintf("not %s", expectation.Caption()),
+		expectation: expectation,
+	}
+}
+
+// notExpectation is an [Expectation] that inverts another expectation.
+type notExpectation struct {
+	caption     string
+	expectation Expectation
+}
+
+func (e *notExpectation) Caption() string {
+	return e.caption
+}
+
+func (e *notExpectation) Predicate(s PredicateScope) (Predicate, error) {
+	p, err := e.expectation.Predicate(s)
+	if err != nil {
+		return nil, err
+	}
+
+	return &notPredicate{
+		expectation: p,
+	}, nil
+}
+
+// notPredicate is the [Predicate] implementation for [notExpectation].
+type notPredicate struct {
+	expectation Predicate
+}
+
+func (p *notPredicate) Notify(f fact.Fact) {
+	p.expectation.Notify(f)
+}
+
+func (p *notPredicate) Ok() bool {
+	return !p.expectation.Ok()
+}
+
+func (p *notPredicate) Done() {
+	p.expectation.Done()
+}
+
+func (p *notPredicate) Report(ctx ReportGenerationContext) *Report {
+	ctx.IsInverted = !ctx.IsInverted
+
+	r := p.expectation.Report(ctx)
+
+	rep := &Report{
+		TreeOk:   ctx.TreeOk,
+		Ok:       p.Ok(),
+		Criteria: "do not " + r.Criteria,
+	}
+
+	return rep
+}
diff --git a/expectation.not_test.go b/expectation.not_test.go
new file mode 100644
index 00000000..2bcc60bb
--- /dev/null
+++ b/expectation.not_test.go
@@ -0,0 +1,106 @@
+package testkit_test
+
+import (
+	"context"
+
+	"github.com/dogmatiq/dogma"
+	. "github.com/dogmatiq/enginekit/enginetest/stubs"
+	. "github.com/dogmatiq/testkit"
+	"github.com/dogmatiq/testkit/internal/testingmock"
+	g "github.com/onsi/ginkgo/v2"
+	gm "github.com/onsi/gomega"
+)
+
+var _ = g.Context("not expectation", func() {
+	var (
+		testingT *testingmock.T
+		app      dogma.Application
+		test     *Test
+	)
+
+	g.BeforeEach(func() {
+		testingT = &testingmock.T{
+			FailSilently: true,
+		}
+
+		app = &ApplicationStub{
+			ConfigureFunc: func(c dogma.ApplicationConfigurer) {
+				c.Identity("<app>", "00df8612-2fd4-4ae3-9acf-afc2b4daf272")
+				c.RegisterIntegration(&IntegrationMessageHandlerStub{
+					ConfigureFunc: func(c dogma.IntegrationConfigurer) {
+						c.Identity("<integration>", "12dfb90b-e47b-4d49-b834-294b01992ad0")
+						c.Routes(
+							dogma.HandlesCommand[CommandStub[TypeA]](),
+							dogma.RecordsEvent[EventStub[TypeA]](),
+						)
+					},
+					HandleCommandFunc: func(
+						_ context.Context,
+						s dogma.IntegrationCommandScope,
+						_ dogma.Command,
+					) error {
+						s.RecordEvent(EventA1)
+						return nil
+					},
+				})
+			},
+		}
+
+		test = Begin(testingT, app).
+			EnableHandlers("<integration>")
+	})
+
+	testExpectationBehavior := func(
+		e Expectation,
+		ok bool,
+		rm reportMatcher,
+	) {
+		test.Expect(ExecuteCommand(CommandA1), e)
+		rm(testingT)
+		gm.Expect(testingT.Failed()).To(gm.Equal(!ok))
+	}
+
+	g.Describe("func Not()", func() {
+		g.DescribeTable(
+			"expectation behavior",
+			testExpectationBehavior,
+			g.Entry(
+				"it fails when the child expectation passes",
+				Not(ToRecordEvent(EventA1)),
+				expectFail,
+				expectReport(
+					`✗ do not record a specific 'stubs.EventStub[TypeA]' event`,
+				),
+			),
+			g.Entry(
+				"it passes when the child expectation fails",
+				Not(ToRecordEvent(EventA2)),
+				expectPass,
+				expectReport(
+					`✓ do not record a specific 'stubs.EventStub[TypeA]' event`,
+				),
+			),
+		)
+
+		g.It("produces the expected caption", func() {
+			test.Expect(
+				noop,
+				Not(ToRecordEvent(EventA2)),
+			)
+
+			gm.Expect(testingT.Logs).To(gm.ContainElement(
+				"--- expect [no-op] not to record a specific 'stubs.EventStub[TypeA]' event ---",
+			))
+		})
+
+		g.It("fails the test if the child cannot construct a predicate", func() {
+			test.Expect(
+				noop,
+				Not(failBeforeAction),
+			)
+
+			gm.Expect(testingT.Logs).To(gm.ContainElement("<always fail before action>"))
+			gm.Expect(testingT.Failed()).To(gm.BeTrue())
+		})
+	})
+})
diff --git a/internal/fixtures/protobuf.pb.go b/internal/fixtures/protobuf.pb.go
index 93d0ea24..40cdbdb9 100644
--- a/internal/fixtures/protobuf.pb.go
+++ b/internal/fixtures/protobuf.pb.go
@@ -1,7 +1,7 @@
 // Code generated by protoc-gen-go. DO NOT EDIT.
 // versions:
 // 	protoc-gen-go v1.34.2
-// 	protoc        v5.27.2
+// 	protoc        v5.27.3
 // source: github.com/dogmatiq/testkit/internal/fixtures/protobuf.proto
 
 package fixtures