diff --git a/hack/dockerfile/install/containerd.installer b/hack/dockerfile/install/containerd.installer
index b7dbb5bf72..cf96e69887 100755
--- a/hack/dockerfile/install/containerd.installer
+++ b/hack/dockerfile/install/containerd.installer
@@ -4,7 +4,7 @@ set -e
 # containerd is also pinned in vendor.conf. When updating the binary
 # version you may also need to update the vendor version to pick up bug
 # fixes or new APIs.
-: "${CONTAINERD_COMMIT:=69107e47a62e1d690afa2b9b1d43f8ece3ff4483}" # v1.5.4
+: "${CONTAINERD_COMMIT:=72cec4be58a9eb6b2910f5d10f1c01ca47d231c0}" # v1.5.5
 
 install_containerd() (
 	echo "Install containerd version $CONTAINERD_COMMIT"
diff --git a/vendor.conf b/vendor.conf
index ac68294fb4..e64f0d9219 100644
--- a/vendor.conf
+++ b/vendor.conf
@@ -128,7 +128,7 @@ github.com/googleapis/gax-go                        bd5b16380fd03dc758d11cef74ba
 google.golang.org/genproto                          3f1135a288c9a07e340ae8ba4cc6c7065a3160e8
 
 # containerd
-github.com/containerd/containerd                    69107e47a62e1d690afa2b9b1d43f8ece3ff4483 # v1.5.4
+github.com/containerd/containerd                    72cec4be58a9eb6b2910f5d10f1c01ca47d231c0 # v1.5.5
 github.com/containerd/fifo                          650e8a8a179d040123db61f016cb133143e7a581 # v1.0.0
 github.com/containerd/continuity                    bce1c3f9669b6f3e7f6656ee715b0b4d75fa64a6 # v0.1.0
 github.com/containerd/cgroups                       b9de8a2212026c07cec67baf3323f1fc0121e048 # v1.0.1
diff --git a/vendor/github.com/containerd/containerd/go.mod b/vendor/github.com/containerd/containerd/go.mod
index c131b72c47..3c32d1eb87 100644
--- a/vendor/github.com/containerd/containerd/go.mod
+++ b/vendor/github.com/containerd/containerd/go.mod
@@ -19,7 +19,7 @@ require (
 	github.com/containerd/typeurl v1.0.2
 	github.com/containerd/zfs v1.0.0
 	github.com/containernetworking/plugins v0.9.1
-	github.com/coreos/go-systemd/v22 v22.1.0
+	github.com/coreos/go-systemd/v22 v22.3.2
 	github.com/davecgh/go-spew v1.1.1
 	github.com/docker/go-events v0.0.0-20190806004212-e31b211e4f1c
 	github.com/docker/go-metrics v0.0.1
@@ -28,8 +28,8 @@ require (
 	github.com/fsnotify/fsnotify v1.4.9
 	github.com/gogo/googleapis v1.4.0
 	github.com/gogo/protobuf v1.3.2
-	github.com/golang/protobuf v1.4.3
-	github.com/google/go-cmp v0.5.4
+	github.com/golang/protobuf v1.5.0
+	github.com/google/go-cmp v0.5.5
 	github.com/google/uuid v1.2.0
 	github.com/grpc-ecosystem/go-grpc-prometheus v1.2.0
 	github.com/hashicorp/go-multierror v1.0.0
@@ -40,22 +40,22 @@ require (
 	github.com/moby/sys/symlink v0.1.0
 	github.com/opencontainers/go-digest v1.0.0
 	github.com/opencontainers/image-spec v1.0.1
-	github.com/opencontainers/runc v1.0.0-rc93
-	github.com/opencontainers/runtime-spec v1.0.3-0.20200929063507-e6143ca7d51d
-	github.com/opencontainers/selinux v1.8.0
+	github.com/opencontainers/runc v1.0.1
+	github.com/opencontainers/runtime-spec v1.0.3-0.20210326190908-1c3f411f0417
+	github.com/opencontainers/selinux v1.8.2
 	github.com/pelletier/go-toml v1.8.1
 	github.com/pkg/errors v0.9.1
 	github.com/prometheus/client_golang v1.7.1
 	github.com/prometheus/procfs v0.6.0 // indirect; temporarily force v0.6.0, which was previously defined in imgcrypt as explicit version
 	github.com/satori/go.uuid v1.2.0 // indirect
-	github.com/sirupsen/logrus v1.7.0
+	github.com/sirupsen/logrus v1.8.1
 	github.com/stretchr/testify v1.6.1
 	github.com/tchap/go-patricia v2.2.6+incompatible
 	github.com/urfave/cli v1.22.2
 	go.etcd.io/bbolt v1.3.5
 	golang.org/x/net v0.0.0-20210226172049-e18ecbb05110
 	golang.org/x/sync v0.0.0-20201207232520-09787c993a3a
-	golang.org/x/sys v0.0.0-20210324051608-47abb6519492
+	golang.org/x/sys v0.0.0-20210426230700-d19ff857e887
 	google.golang.org/grpc v1.33.2
 	gotest.tools/v3 v3.0.3
 	k8s.io/api v0.20.6
diff --git a/vendor/github.com/containerd/containerd/remotes/docker/fetcher.go b/vendor/github.com/containerd/containerd/remotes/docker/fetcher.go
index 9d6708def1..5796fbf4a1 100644
--- a/vendor/github.com/containerd/containerd/remotes/docker/fetcher.go
+++ b/vendor/github.com/containerd/containerd/remotes/docker/fetcher.go
@@ -148,7 +148,7 @@ func (r dockerFetcher) Fetch(ctx context.Context, desc ocispec.Descriptor) (io.R
 	})
 }
 
-func (r dockerFetcher) open(ctx context.Context, req *request, mediatype string, offset int64) (io.ReadCloser, error) {
+func (r dockerFetcher) open(ctx context.Context, req *request, mediatype string, offset int64) (_ io.ReadCloser, retErr error) {
 	req.header.Set("Accept", strings.Join([]string{mediatype, `*/*`}, ", "))
 
 	if offset > 0 {
@@ -162,13 +162,17 @@ func (r dockerFetcher) open(ctx context.Context, req *request, mediatype string,
 	if err != nil {
 		return nil, err
 	}
+	defer func() {
+		if retErr != nil {
+			resp.Body.Close()
+		}
+	}()
 
 	if resp.StatusCode > 299 {
 		// TODO(stevvooe): When doing a offset specific request, we should
 		// really distinguish between a 206 and a 200. In the case of 200, we
 		// can discard the bytes, hiding the seek behavior from the
 		// implementation.
-		defer resp.Body.Close()
 
 		if resp.StatusCode == http.StatusNotFound {
 			return nil, errors.Wrapf(errdefs.ErrNotFound, "content at %v not found", req.String())
diff --git a/vendor/github.com/containerd/containerd/remotes/docker/pusher.go b/vendor/github.com/containerd/containerd/remotes/docker/pusher.go
index eae5a251d9..97ed66a6ab 100644
--- a/vendor/github.com/containerd/containerd/remotes/docker/pusher.go
+++ b/vendor/github.com/containerd/containerd/remotes/docker/pusher.go
@@ -143,13 +143,16 @@ func (p dockerPusher) push(ctx context.Context, desc ocispec.Descriptor, ref str
 						// TODO: Set updated time?
 					},
 				})
+				resp.Body.Close()
 				return nil, errors.Wrapf(errdefs.ErrAlreadyExists, "content %v on remote", desc.Digest)
 			}
 		} else if resp.StatusCode != http.StatusNotFound {
 			err := remoteserrors.NewUnexpectedStatusErr(resp)
 			log.G(ctx).WithField("resp", resp).WithField("body", string(err.(remoteserrors.ErrUnexpectedStatus).Body)).Debug("unexpected response")
+			resp.Body.Close()
 			return nil, err
 		}
+		resp.Body.Close()
 	}
 
 	if isManifest {
diff --git a/vendor/github.com/containerd/containerd/remotes/docker/resolver.go b/vendor/github.com/containerd/containerd/remotes/docker/resolver.go
index 866379eb86..1be9e1d05c 100644
--- a/vendor/github.com/containerd/containerd/remotes/docker/resolver.go
+++ b/vendor/github.com/containerd/containerd/remotes/docker/resolver.go
@@ -229,10 +229,10 @@ func (r *dockerResolver) Resolve(ctx context.Context, ref string) (string, ocisp
 	}
 
 	var (
-		lastErr error
-		paths   [][]string
-		dgst    = refspec.Digest()
-		caps    = HostCapabilityPull
+		firstErr error
+		paths    [][]string
+		dgst     = refspec.Digest()
+		caps     = HostCapabilityPull
 	)
 
 	if dgst != "" {
@@ -283,8 +283,8 @@ func (r *dockerResolver) Resolve(ctx context.Context, ref string) (string, ocisp
 					err = errors.Wrapf(err, "pull access denied, repository does not exist or may require authorization")
 				}
 				// Store the error for referencing later
-				if lastErr == nil {
-					lastErr = err
+				if firstErr == nil {
+					firstErr = err
 				}
 				log.G(ctx).WithError(err).Info("trying next host")
 				continue // try another host
@@ -296,7 +296,14 @@ func (r *dockerResolver) Resolve(ctx context.Context, ref string) (string, ocisp
 					log.G(ctx).Info("trying next host - response was http.StatusNotFound")
 					continue
 				}
-				return "", ocispec.Descriptor{}, errors.Errorf("unexpected status code %v: %v", u, resp.Status)
+				if resp.StatusCode > 399 {
+					// Set firstErr when encountering the first non-404 status code.
+					if firstErr == nil {
+						firstErr = errors.Errorf("pulling from host %s failed with status code %v: %v", host.Host, u, resp.Status)
+					}
+					continue // try another host
+				}
+				return "", ocispec.Descriptor{}, errors.Errorf("pulling from host %s failed with unexpected status code %v: %v", host.Host, u, resp.Status)
 			}
 			size := resp.ContentLength
 			contentType := getManifestMediaType(resp)
@@ -359,8 +366,8 @@ func (r *dockerResolver) Resolve(ctx context.Context, ref string) (string, ocisp
 			}
 			// Prevent resolving to excessively large manifests
 			if size > MaxManifestSize {
-				if lastErr == nil {
-					lastErr = errors.Wrapf(errdefs.ErrNotFound, "rejecting %d byte manifest for %s", size, ref)
+				if firstErr == nil {
+					firstErr = errors.Wrapf(errdefs.ErrNotFound, "rejecting %d byte manifest for %s", size, ref)
 				}
 				continue
 			}
@@ -376,11 +383,15 @@ func (r *dockerResolver) Resolve(ctx context.Context, ref string) (string, ocisp
 		}
 	}
 
-	if lastErr == nil {
-		lastErr = errors.Wrap(errdefs.ErrNotFound, ref)
+	// If above loop terminates without return, then there was an error.
+	// "firstErr" contains the first non-404 error. That is, "firstErr == nil"
+	// means that either no registries were given or each registry returned 404.
+
+	if firstErr == nil {
+		firstErr = errors.Wrap(errdefs.ErrNotFound, ref)
 	}
 
-	return "", ocispec.Descriptor{}, lastErr
+	return "", ocispec.Descriptor{}, firstErr
 }
 
 func (r *dockerResolver) Fetcher(ctx context.Context, ref string) (remotes.Fetcher, error) {
@@ -539,7 +550,21 @@ func (r *request) do(ctx context.Context) (*http.Response, error) {
 	if err := r.authorize(ctx, req); err != nil {
 		return nil, errors.Wrap(err, "failed to authorize")
 	}
-	resp, err := ctxhttp.Do(ctx, r.host.Client, req)
+
+	var client = &http.Client{}
+	if r.host.Client != nil {
+		*client = *r.host.Client
+	}
+	if client.CheckRedirect == nil {
+		client.CheckRedirect = func(req *http.Request, via []*http.Request) error {
+			if len(via) >= 10 {
+				return errors.New("stopped after 10 redirects")
+			}
+			return errors.Wrap(r.authorize(ctx, req), "failed to authorize redirect")
+		}
+	}
+
+	resp, err := ctxhttp.Do(ctx, client, req)
 	if err != nil {
 		return nil, errors.Wrap(err, "failed to do request")
 	}
diff --git a/vendor/github.com/containerd/containerd/version/version.go b/vendor/github.com/containerd/containerd/version/version.go
index 4f8986230c..9b53cb13e9 100644
--- a/vendor/github.com/containerd/containerd/version/version.go
+++ b/vendor/github.com/containerd/containerd/version/version.go
@@ -23,7 +23,7 @@ var (
 	Package = "github.com/containerd/containerd"
 
 	// Version holds the complete version number. Filled in at linking time.
-	Version = "1.5.4+unknown"
+	Version = "1.5.5+unknown"
 
 	// Revision is filled with the VCS (e.g. git) revision being used to build
 	// the program at linking time.