diff --git a/.changelog/3299.txt b/.changelog/3299.txt
new file mode 100644
index 0000000000..c0e2d5195f
--- /dev/null
+++ b/.changelog/3299.txt
@@ -0,0 +1,3 @@
+```release-note:bug
+provider: Fixed an error with resources failing to upload large files (e.g. with `google_storage_bucket_object`) during retried requests
+```
diff --git a/google-beta/retry_transport.go b/google-beta/retry_transport.go
index c1019c8aa5..ed05c1479e 100644
--- a/google-beta/retry_transport.go
+++ b/google-beta/retry_transport.go
@@ -34,7 +34,6 @@ import (
 	"context"
 	"errors"
 	"fmt"
-	"github.com/hashicorp/errwrap"
 	"github.com/hashicorp/terraform-plugin-sdk/helper/resource"
 	"google.golang.org/api/googleapi"
 	"io/ioutil"
@@ -99,19 +98,29 @@ func (t *retryTransport) RoundTrip(req *http.Request) (resp *http.Response, resp
 	backoff := time.Millisecond * 500
 	nextBackoff := time.Millisecond * 500
 
+	// VCR depends on the original request body being consumed, so
+	// consume here. Since this won't affect the request itself,
+	// we do this before the actual Retry loop so we can consume the request Body as needed
+	// e.g. if the request couldn't be retried, we use the original request
+	if _, err := httputil.DumpRequestOut(req, true); err != nil {
+		log.Printf("[WARN] Retry Transport: Consuming original request body failed: %v", err)
+	}
+
 	log.Printf("[DEBUG] Retry Transport: starting RoundTrip retry loop")
 Retry:
 	for {
-		log.Printf("[DEBUG] Retry Transport: request attempt %d", attempts)
-
-		// Copy the request - we dont want to use the original request as
-		// RoundTrip contract says request body can/will be consumed
+		// RoundTrip contract says request body can/will be consumed, so we need to
+		// copy the request body for each attempt.
+		// If we can't copy the request, we run as a single request.
 		newRequest, copyErr := copyHttpRequest(req)
 		if copyErr != nil {
-			respErr = errwrap.Wrapf("unable to copy invalid http.Request for retry: {{err}}", copyErr)
+			log.Printf("[WARN] Retry Transport: Unable to copy request body: %v.", copyErr)
+			log.Printf("[WARN] Retry Transport: Running request as non-retryable")
+			resp, respErr = t.internal.RoundTrip(req)
 			break Retry
 		}
 
+		log.Printf("[DEBUG] Retry Transport: request attempt %d", attempts)
 		// Do the wrapped Roundtrip. This is one request in the retry loop.
 		resp, respErr = t.internal.RoundTrip(newRequest)
 		attempts++
@@ -141,13 +150,6 @@ Retry:
 			continue
 		}
 	}
-
-	// VCR depends on the original request body being consumed, so consume it here
-	_, err := httputil.DumpRequestOut(req, true)
-	if err != nil {
-		log.Printf("[DEBUG] Retry Transport: Reading request failed: %v", err)
-	}
-
 	log.Printf("[DEBUG] Retry Transport: Returning after %d attempts", attempts)
 	return resp, respErr
 }
@@ -157,15 +159,13 @@ Retry:
 // so it can be consumed.
 func copyHttpRequest(req *http.Request) (*http.Request, error) {
 	newRequest := *req
-
 	if req.Body == nil || req.Body == http.NoBody {
 		return &newRequest, nil
 	}
-
 	// Helpers like http.NewRequest add a GetBody for copying.
 	// If not given, we should reject the request.
 	if req.GetBody == nil {
-		return nil, errors.New("invalid HTTP request for transport, expected request.GetBody for non-empty Body")
+		return nil, errors.New("request.GetBody is not defined for non-empty Body")
 	}
 
 	bd, err := req.GetBody()
diff --git a/google-beta/retry_transport_test.go b/google-beta/retry_transport_test.go
index 617528ca5f..4c8ba023ec 100644
--- a/google-beta/retry_transport_test.go
+++ b/google-beta/retry_transport_test.go
@@ -123,6 +123,51 @@ func TestRetryTransport_SuccessWithBody(t *testing.T) {
 	testRetryTransport_checkBody(t, resp, body)
 }
 
+// Check for no and no retries if the request has no getBody (it should only run once)
+func TestRetryTransport_DoesNotRetryEmptyGetBody(t *testing.T) {
+	msg := "non empty body"
+	attempted := false
+
+	ts, client := setUpRetryTransportServerClient(http.HandlerFunc(
+		func(w http.ResponseWriter, r *http.Request) {
+			// Check for request body
+			dump, err := ioutil.ReadAll(r.Body)
+			if err != nil {
+				w.WriteHeader(testRetryTransportCodeFailure)
+				if _, werr := w.Write([]byte(fmt.Sprintf("got error: %v", err))); werr != nil {
+					t.Errorf("[ERROR] unable to write to response writer: %v", err)
+				}
+			}
+			dumpS := string(dump)
+			if dumpS != msg {
+				w.WriteHeader(testRetryTransportCodeFailure)
+				if _, werr := w.Write([]byte(fmt.Sprintf("got unexpected body: %s", dumpS))); werr != nil {
+					t.Errorf("[ERROR] unable to write to response writer: %v", err)
+				}
+			}
+			if attempted {
+				w.WriteHeader(testRetryTransportCodeFailure)
+				if _, werr := w.Write([]byte("expected only one try")); werr != nil {
+					t.Errorf("[ERROR] unable to write to response writer: %v", err)
+				}
+			}
+			attempted = true
+			w.WriteHeader(testRetryTransportCodeRetry)
+		}))
+	defer ts.Close()
+
+	// Create request
+	req, err := http.NewRequest("GET", ts.URL, strings.NewReader(msg))
+	if err != nil {
+		t.Errorf("[ERROR] unable to make test request: %v", err)
+	}
+	// remove GetBody
+	req.GetBody = nil
+
+	resp, err := client.Do(req)
+	testRetryTransport_checkFailedWhileRetrying(t, resp, err)
+}
+
 // handlers
 func testRetryTransportHandler_noRetries(t *testing.T, code int) http.Handler {
 	return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {