diff --git a/pkg/plugin/installer/http_installer.go b/pkg/plugin/installer/http_installer.go
index 28e50b72b..bcbcbde93 100644
--- a/pkg/plugin/installer/http_installer.go
+++ b/pkg/plugin/installer/http_installer.go
@@ -59,6 +59,18 @@ var Extractors = map[string]Extractor{
 	".tgz":    &TarGzExtractor{},
 }
 
+// Convert a media type to an extractor extension.
+//
+// This should be refactored in Helm 4, combined with the extension-based mechanism.
+func mediaTypeToExtension(mt string) (string, bool) {
+	switch strings.ToLower(mt) {
+	case "application/gzip", "application/x-gzip", "application/x-tgz", "application/x-gtar":
+		return ".tgz", true
+	default:
+		return "", false
+	}
+}
+
 // NewExtractor creates a new extractor matching the source file name
 func NewExtractor(source string) (Extractor, error) {
 	for suffix, extractor := range Extractors {
diff --git a/pkg/plugin/installer/http_installer_test.go b/pkg/plugin/installer/http_installer_test.go
index 3eb92ee77..e89fea29d 100644
--- a/pkg/plugin/installer/http_installer_test.go
+++ b/pkg/plugin/installer/http_installer_test.go
@@ -20,9 +20,13 @@ import (
 	"bytes"
 	"compress/gzip"
 	"encoding/base64"
+	"fmt"
 	"io/ioutil"
+	"net/http"
+	"net/http/httptest"
 	"os"
 	"path/filepath"
+	"strings"
 	"syscall"
 	"testing"
 
@@ -63,9 +67,24 @@ func TestStripName(t *testing.T) {
 	}
 }
 
+func mockArchiveServer() *httptest.Server {
+	return httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		if !strings.HasSuffix(r.URL.Path, ".tar.gz") {
+			w.Header().Add("Content-Type", "text/html")
+			fmt.Fprintln(w, "broken")
+			return
+		}
+		w.Header().Add("Content-Type", "application/gzip")
+		fmt.Fprintln(w, "test")
+	}))
+}
+
 func TestHTTPInstaller(t *testing.T) {
 	defer ensure.HelmHome(t)()
-	source := "https://repo.localdomain/plugins/fake-plugin-0.0.1.tar.gz"
+
+	srv := mockArchiveServer()
+	defer srv.Close()
+	source := srv.URL + "/plugins/fake-plugin-0.0.1.tar.gz"
 
 	if err := os.MkdirAll(helmpath.DataPath("plugins"), 0755); err != nil {
 		t.Fatalf("Could not create %s: %s", helmpath.DataPath("plugins"), err)
@@ -111,7 +130,9 @@ func TestHTTPInstaller(t *testing.T) {
 
 func TestHTTPInstallerNonExistentVersion(t *testing.T) {
 	defer ensure.HelmHome(t)()
-	source := "https://repo.localdomain/plugins/fake-plugin-0.0.2.tar.gz"
+	srv := mockArchiveServer()
+	defer srv.Close()
+	source := srv.URL + "/plugins/fake-plugin-0.0.1.tar.gz"
 
 	if err := os.MkdirAll(helmpath.DataPath("plugins"), 0755); err != nil {
 		t.Fatalf("Could not create %s: %s", helmpath.DataPath("plugins"), err)
@@ -141,7 +162,9 @@ func TestHTTPInstallerNonExistentVersion(t *testing.T) {
 }
 
 func TestHTTPInstallerUpdate(t *testing.T) {
-	source := "https://repo.localdomain/plugins/fake-plugin-0.0.1.tar.gz"
+	srv := mockArchiveServer()
+	defer srv.Close()
+	source := srv.URL + "/plugins/fake-plugin-0.0.1.tar.gz"
 	defer ensure.HelmHome(t)()
 
 	if err := os.MkdirAll(helmpath.DataPath("plugins"), 0755); err != nil {
@@ -307,3 +330,26 @@ func TestCleanJoin(t *testing.T) {
 	}
 
 }
+
+func TestMediaTypeToExtension(t *testing.T) {
+
+	for mt, shouldPass := range map[string]bool{
+		"":                   false,
+		"application/gzip":   true,
+		"application/x-gzip": true,
+		"application/x-tgz":  true,
+		"application/x-gtar": true,
+		"application/json":   false,
+	} {
+		ext, ok := mediaTypeToExtension(mt)
+		if ok != shouldPass {
+			t.Errorf("Media type %q failed test", mt)
+		}
+		if shouldPass && ext == "" {
+			t.Errorf("Expected an extension but got empty string")
+		}
+		if !shouldPass && len(ext) != 0 {
+			t.Error("Expected extension to be empty for unrecognized type")
+		}
+	}
+}
diff --git a/pkg/plugin/installer/installer.go b/pkg/plugin/installer/installer.go
index 61b49ab3b..6f01494e5 100644
--- a/pkg/plugin/installer/installer.go
+++ b/pkg/plugin/installer/installer.go
@@ -18,6 +18,7 @@ package installer
 import (
 	"fmt"
 	"log"
+	"net/http"
 	"os"
 	"path/filepath"
 	"strings"
@@ -89,10 +90,29 @@ func isLocalReference(source string) bool {
 }
 
 // isRemoteHTTPArchive checks if the source is a http/https url and is an archive
+//
+// It works by checking whether the source looks like a URL and, if it does, running a
+// HEAD operation to see if the remote resource is a file that we understand.
 func isRemoteHTTPArchive(source string) bool {
 	if strings.HasPrefix(source, "http://") || strings.HasPrefix(source, "https://") {
+		res, err := http.Head(source)
+		if err != nil {
+			// If we get an error at the network layer, we can't install it. So
+			// we return false.
+			return false
+		}
+
+		// Next, we look for the content type or content disposition headers to see
+		// if they have matching extractors.
+		contentType := res.Header.Get("content-type")
+		foundSuffix, ok := mediaTypeToExtension(contentType)
+		if !ok {
+			// Media type not recognized
+			return false
+		}
+
 		for suffix := range Extractors {
-			if strings.HasSuffix(source, suffix) {
+			if strings.HasSuffix(foundSuffix, suffix) {
 				return true
 			}
 		}
diff --git a/pkg/plugin/installer/installer_test.go b/pkg/plugin/installer/installer_test.go
new file mode 100644
index 000000000..a11464924
--- /dev/null
+++ b/pkg/plugin/installer/installer_test.go
@@ -0,0 +1,40 @@
+/*
+Copyright The Helm Authors.
+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 installer
+
+import "testing"
+
+func TestIsRemoteHTTPArchive(t *testing.T) {
+	srv := mockArchiveServer()
+	defer srv.Close()
+	source := srv.URL + "/plugins/fake-plugin-0.0.1.tar.gz"
+
+	if isRemoteHTTPArchive("/not/a/URL") {
+		t.Errorf("Expected non-URL to return false")
+	}
+
+	if isRemoteHTTPArchive("https://127.0.0.1:123/fake/plugin-1.2.3.tgz") {
+		t.Errorf("Bad URL should not have succeeded.")
+	}
+
+	if !isRemoteHTTPArchive(source) {
+		t.Errorf("Expected %q to be a valid archive URL", source)
+	}
+
+	if isRemoteHTTPArchive(source + "-not-an-extension") {
+		t.Error("Expected media type match to fail")
+	}
+}