diff --git a/internal/initwd/module_install.go b/internal/initwd/module_install.go
index cbfd8e98c..38a44c262 100644
--- a/internal/initwd/module_install.go
+++ b/internal/initwd/module_install.go
@@ -438,8 +438,8 @@ func (i *ModuleInstaller) installRegistryModule(req *earlyconfig.ModuleRequest,
 			log.Printf("[ERROR] %s from %s %s: %s", key, addr, latestMatch, err)
 			diags = diags.Append(tfdiags.Sourceless(
 				tfdiags.Error,
-				"Invalid response from remote module registry",
-				fmt.Sprintf("The remote registry at %s failed to return a download URL for %s %s.", hostname, addr, latestMatch),
+				"Error accessing remote module registry",
+				fmt.Sprintf("Failed to retrieve a download URL for %s %s from %s: %s", addr, latestMatch, hostname, err),
 			))
 			return nil, nil, diags
 		}
diff --git a/registry/client.go b/registry/client.go
index e8f7ac111..dcbb0debb 100644
--- a/registry/client.go
+++ b/registry/client.go
@@ -7,10 +7,13 @@ import (
 	"log"
 	"net/http"
 	"net/url"
+	"os"
 	"path"
+	"strconv"
 	"strings"
 	"time"
 
+	"github.com/hashicorp/go-retryablehttp"
 	"github.com/hashicorp/terraform-svchost"
 	"github.com/hashicorp/terraform-svchost/disco"
 	"github.com/hashicorp/terraform/httpclient"
@@ -25,18 +28,34 @@ const (
 	requestTimeout     = 10 * time.Second
 	modulesServiceID   = "modules.v1"
 	providersServiceID = "providers.v1"
+
+	// registryDiscoveryRetryEnvName is the name of the environment variable that
+	// can be configured to customize number of retries for module and provider
+	// discovery requests with the remote registry.
+	registryDiscoveryRetryEnvName = "TF_REGISTRY_DISCOVERY_RETRY"
+	defaultRetry                  = 1
 )
 
+var discoveryRetry int
+
 var tfVersion = version.String()
 
+func init() {
+	configureDiscoveryRetry()
+}
+
 // Client provides methods to query Terraform Registries.
 type Client struct {
 	// this is the client to be used for all requests.
-	client *http.Client
+	client *retryablehttp.Client
 
 	// services is a required *disco.Disco, which may have services and
 	// credentials pre-loaded.
 	services *disco.Disco
+
+	// retry is the number of retries the client will attempt for each request
+	// if it runs into a transient failure with the remote registry.
+	retry int
 }
 
 // NewClient returns a new initialized registry client.
@@ -49,13 +68,18 @@ func NewClient(services *disco.Disco, client *http.Client) *Client {
 		client = httpclient.New()
 		client.Timeout = requestTimeout
 	}
+	retryableClient := retryablehttp.NewClient()
+	retryableClient.HTTPClient = client
+	retryableClient.RetryMax = discoveryRetry
+	retryableClient.RequestLogHook = requestLogHook
+	retryableClient.ErrorHandler = maxRetryErrorHandler
 
-	services.Transport = client.Transport
+	services.Transport = retryableClient.HTTPClient.Transport
 
 	services.SetUserAgent(httpclient.TerraformUserAgent(version.String()))
 
 	return &Client{
-		client:   client,
+		client:   retryableClient,
 		services: services,
 	}
 }
@@ -93,12 +117,12 @@ func (c *Client) ModuleVersions(module *regsrc.Module) (*response.ModuleVersions
 
 	log.Printf("[DEBUG] fetching module versions from %q", service)
 
-	req, err := http.NewRequest("GET", service.String(), nil)
+	req, err := retryablehttp.NewRequest("GET", service.String(), nil)
 	if err != nil {
 		return nil, err
 	}
 
-	c.addRequestCreds(host, req)
+	c.addRequestCreds(host, req.Request)
 	req.Header.Set(xTerraformVersion, tfVersion)
 
 	resp, err := c.client.Do(req)
@@ -170,12 +194,12 @@ func (c *Client) ModuleLocation(module *regsrc.Module, version string) (string,
 
 	log.Printf("[DEBUG] looking up module location from %q", download)
 
-	req, err := http.NewRequest("GET", download.String(), nil)
+	req, err := retryablehttp.NewRequest("GET", download.String(), nil)
 	if err != nil {
 		return "", err
 	}
 
-	c.addRequestCreds(host, req)
+	c.addRequestCreds(host, req.Request)
 	req.Header.Set(xTerraformVersion, tfVersion)
 
 	resp, err := c.client.Do(req)
@@ -250,12 +274,12 @@ func (c *Client) TerraformProviderVersions(provider *regsrc.TerraformProvider) (
 
 	log.Printf("[DEBUG] fetching provider versions from %q", service)
 
-	req, err := http.NewRequest("GET", service.String(), nil)
+	req, err := retryablehttp.NewRequest("GET", service.String(), nil)
 	if err != nil {
 		return nil, err
 	}
 
-	c.addRequestCreds(host, req)
+	c.addRequestCreds(host, req.Request)
 	req.Header.Set(xTerraformVersion, tfVersion)
 
 	resp, err := c.client.Do(req)
@@ -310,12 +334,12 @@ func (c *Client) TerraformProviderLocation(provider *regsrc.TerraformProvider, v
 
 	log.Printf("[DEBUG] fetching provider location from %q", service)
 
-	req, err := http.NewRequest("GET", service.String(), nil)
+	req, err := retryablehttp.NewRequest("GET", service.String(), nil)
 	if err != nil {
 		return nil, err
 	}
 
-	c.addRequestCreds(host, req)
+	c.addRequestCreds(host, req.Request)
 	req.Header.Set(xTerraformVersion, tfVersion)
 
 	resp, err := c.client.Do(req)
@@ -343,3 +367,37 @@ func (c *Client) TerraformProviderLocation(provider *regsrc.TerraformProvider, v
 
 	return &loc, nil
 }
+
+func configureDiscoveryRetry() {
+	discoveryRetry = defaultRetry
+
+	if v := os.Getenv(registryDiscoveryRetryEnvName); v != "" {
+		retry, err := strconv.Atoi(v)
+		if err == nil && retry > 0 {
+			discoveryRetry = retry
+		}
+	}
+}
+
+func requestLogHook(logger retryablehttp.Logger, req *http.Request, i int) {
+	if i > 0 {
+		logger.Printf("[INFO] Previous request to the remote registry failed, attempting retry.")
+	}
+}
+
+func maxRetryErrorHandler(resp *http.Response, err error, numTries int) (*http.Response, error) {
+	// Close the body per library instructions
+	if resp != nil {
+		resp.Body.Close()
+	}
+
+	var errMsg string
+	if err != nil {
+		errMsg = fmt.Sprintf(" %s", err)
+	}
+	if numTries > 1 {
+		return resp, fmt.Errorf("the request failed after %d attempts, please try again later: %d%s",
+			numTries, resp.StatusCode, errMsg)
+	}
+	return resp, fmt.Errorf("the request failed, please try again later: %d%s", resp.StatusCode, errMsg)
+}
diff --git a/registry/client_test.go b/registry/client_test.go
index 105205f94..f3a2bbcc3 100644
--- a/registry/client_test.go
+++ b/registry/client_test.go
@@ -1,7 +1,9 @@
 package registry
 
 import (
+	"context"
 	"fmt"
+	"net/http"
 	"os"
 	"strings"
 	"testing"
@@ -14,6 +16,42 @@ import (
 	tfversion "github.com/hashicorp/terraform/version"
 )
 
+func TestConfigureDiscoveryRetry(t *testing.T) {
+	t.Run("default retry", func(t *testing.T) {
+		if discoveryRetry != defaultRetry {
+			t.Fatalf("expected retry %q, got %q", defaultRetry, discoveryRetry)
+		}
+
+		rc := NewClient(nil, nil)
+		if rc.client.RetryMax != defaultRetry {
+			t.Fatalf("expected client retry %q, got %q",
+				defaultRetry, rc.client.RetryMax)
+		}
+	})
+
+	t.Run("configured retry", func(t *testing.T) {
+		defer func() {
+			os.Setenv(registryDiscoveryRetryEnvName,
+				os.Getenv(registryDiscoveryRetryEnvName))
+			discoveryRetry = defaultRetry
+		}()
+		os.Setenv(registryDiscoveryRetryEnvName, "2")
+
+		configureDiscoveryRetry()
+		expected := 2
+		if discoveryRetry != expected {
+			t.Fatalf("expected retry %q, got %q",
+				expected, discoveryRetry)
+		}
+
+		rc := NewClient(nil, nil)
+		if rc.client.RetryMax != expected {
+			t.Fatalf("expected client retry %q, got %q",
+				expected, rc.client.RetryMax)
+		}
+	})
+}
+
 func TestLookupModuleVersions(t *testing.T) {
 	server := test.Registry()
 	defer server.Close()
@@ -179,20 +217,31 @@ func TestAccLookupModuleVersions(t *testing.T) {
 	}
 }
 
-// the error should reference the config source exatly, not the discovered path.
+// the error should reference the config source exactly, not the discovered path.
 func TestLookupLookupModuleError(t *testing.T) {
 	server := test.Registry()
 	defer server.Close()
 
 	client := NewClient(test.Disco(server), nil)
 
-	// this should not be found in teh registry
+	// this should not be found in the registry
 	src := "bad/local/path"
 	mod, err := regsrc.ParseModuleSource(src)
 	if err != nil {
 		t.Fatal(err)
 	}
 
+	// Instrument CheckRetry to make sure 404s are not retried
+	retries := 0
+	oldCheck := client.client.CheckRetry
+	client.client.CheckRetry = func(ctx context.Context, resp *http.Response, err error) (bool, error) {
+		if retries > 0 {
+			t.Fatal("retried after module not found")
+		}
+		retries++
+		return oldCheck(ctx, resp, err)
+	}
+
 	_, err = client.ModuleLocation(mod, "0.2.0")
 	if err == nil {
 		t.Fatal("expected error")
@@ -204,6 +253,31 @@ func TestLookupLookupModuleError(t *testing.T) {
 	}
 }
 
+func TestLookupModuleRetryError(t *testing.T) {
+	server := test.RegistryRetryableErrorsServer()
+	defer server.Close()
+
+	client := NewClient(test.Disco(server), nil)
+
+	src := "example.com/test-versions/name/provider"
+	modsrc, err := regsrc.ParseModuleSource(src)
+	if err != nil {
+		t.Fatal(err)
+	}
+	resp, err := client.ModuleVersions(modsrc)
+	if err == nil {
+		t.Fatal("expected requests to exceed retry", err)
+	}
+	if resp != nil {
+		t.Fatal("unexpected response", *resp)
+	}
+
+	// verify maxRetryErrorHandler handler returned the error
+	if !strings.Contains(err.Error(), "the request failed after 2 attempts, please try again later") {
+		t.Fatal("unexpected error, got:", err)
+	}
+}
+
 func TestLookupProviderVersions(t *testing.T) {
 	server := test.Registry()
 	defer server.Close()
diff --git a/registry/test/mock_registry.go b/registry/test/mock_registry.go
index e1b6249e3..924365f2b 100644
--- a/registry/test/mock_registry.go
+++ b/registry/test/mock_registry.go
@@ -363,3 +363,16 @@ func mockRegHandler() http.Handler {
 func Registry() *httptest.Server {
 	return httptest.NewServer(mockRegHandler())
 }
+
+// RegistryRetryableErrorsServer returns an httptest server that mocks out the
+// registry API to return 502 errors.
+func RegistryRetryableErrorsServer() *httptest.Server {
+	mux := http.NewServeMux()
+	mux.HandleFunc("/v1/modules/", func(w http.ResponseWriter, r *http.Request) {
+		http.Error(w, "mocked server error", http.StatusBadGateway)
+	})
+	mux.HandleFunc("/v1/providers/", func(w http.ResponseWriter, r *http.Request) {
+		http.Error(w, "mocked server error", http.StatusBadGateway)
+	})
+	return httptest.NewServer(mux)
+}