diff --git a/pkg/controller/acmechallenges/sync.go b/pkg/controller/acmechallenges/sync.go
index 5114f4cda..c5e492e00 100644
--- a/pkg/controller/acmechallenges/sync.go
+++ b/pkg/controller/acmechallenges/sync.go
@@ -18,6 +18,7 @@ package acmechallenges
 
 import (
 	"context"
+	"errors"
 	"fmt"
 
 	acmeapi "golang.org/x/crypto/acme"
@@ -300,11 +301,23 @@ func (c *controller) syncChallengeStatus(ctx context.Context, cl acmecl.Interfac
 		return fmt.Errorf("challenge URL is blank - challenge has not been created yet")
 	}
 
-	acmeChallenge, err := cl.GetChallenge(ctx, ch.Spec.URL)
+	acmeAuthorization, err := cl.GetAuthorization(ctx, ch.Spec.AuthorizationURL)
 	if err != nil {
 		return err
 	}
 
+	var acmeChallenge *acmeapi.Challenge
+	for _, challenge := range acmeAuthorization.Challenges {
+		if challenge.URI == ch.Spec.URL {
+			acmeChallenge = challenge
+			break
+		}
+	}
+
+	if acmeChallenge == nil {
+		return errors.New("challenge was not present in authorization")
+	}
+
 	// TODO: should we validate the State returned by the ACME server here?
 	cmState := cmacme.State(acmeChallenge.Status)
 	// be nice to our users and check if there is an error that we
diff --git a/pkg/controller/acmechallenges/sync_test.go b/pkg/controller/acmechallenges/sync_test.go
index 45103914e..a31fbb0bf 100644
--- a/pkg/controller/acmechallenges/sync_test.go
+++ b/pkg/controller/acmechallenges/sync_test.go
@@ -86,6 +86,61 @@ func TestSyncHappyPath(t *testing.T) {
 	)
 
 	tests := map[string]testT{
+		"if GetAuthorization doesn't return challenge, error": {
+			challenge: gen.ChallengeFrom(baseChallenge,
+				gen.SetChallengeProcessing(true),
+				gen.SetChallengeURL("testurl"),
+			),
+			builder: &testpkg.Builder{
+				CertManagerObjects: []runtime.Object{gen.ChallengeFrom(baseChallenge,
+					gen.SetChallengeProcessing(true),
+					gen.SetChallengeURL("testurl"),
+				), testIssuerHTTP01Enabled},
+				ExpectedActions: []testpkg.Action{},
+			},
+			expectErr: true,
+			acmeClient: &acmecl.FakeACME{
+				FakeGetAuthorization: func(ctx context.Context, url string) (*acmeapi.Authorization, error) {
+					return &acmeapi.Authorization{
+						Challenges: []*acmeapi.Challenge{
+							{URI: "foo", Status: acmeapi.StatusPending},
+						},
+					}, nil
+				},
+			},
+		},
+		"if GetAuthorization returns challenge ready, update ready": {
+			challenge: gen.ChallengeFrom(baseChallenge,
+				gen.SetChallengeProcessing(true),
+				gen.SetChallengeURL("testurl"),
+			),
+			builder: &testpkg.Builder{
+				CertManagerObjects: []runtime.Object{gen.ChallengeFrom(baseChallenge,
+					gen.SetChallengeProcessing(true),
+					gen.SetChallengeURL("testurl"),
+				), testIssuerHTTP01Enabled},
+				ExpectedActions: []testpkg.Action{
+					testpkg.NewAction(
+						coretesting.NewUpdateSubresourceAction(cmacme.SchemeGroupVersion.WithResource("challenges"),
+							"status",
+							gen.DefaultTestNamespace,
+							gen.ChallengeFrom(baseChallenge,
+								gen.SetChallengeProcessing(true),
+								gen.SetChallengeURL("testurl"),
+								gen.SetChallengeState(cmacme.Ready),
+							))),
+				},
+			},
+			acmeClient: &acmecl.FakeACME{
+				FakeGetAuthorization: func(ctx context.Context, url string) (*acmeapi.Authorization, error) {
+					return &acmeapi.Authorization{
+						Challenges: []*acmeapi.Challenge{
+							{URI: "testurl", Status: acmeapi.StatusReady},
+						},
+					}, nil
+				},
+			},
+		},
 		"update status if state is unknown": {
 			challenge: gen.ChallengeFrom(baseChallenge,
 				gen.SetChallengeProcessing(true),
@@ -109,8 +164,12 @@ func TestSyncHappyPath(t *testing.T) {
 				},
 			},
 			acmeClient: &acmecl.FakeACME{
-				FakeGetChallenge: func(ctx context.Context, url string) (*acmeapi.Challenge, error) {
-					return &acmeapi.Challenge{Status: acmeapi.StatusPending}, nil
+				FakeGetAuthorization: func(ctx context.Context, url string) (*acmeapi.Authorization, error) {
+					return &acmeapi.Authorization{
+						Challenges: []*acmeapi.Challenge{
+							{URI: "testurl", Status: acmeapi.StatusPending},
+						},
+					}, nil
 				},
 			},
 		},