diff --git a/client.go b/client.go
index cda0210..9ecab4f 100644
--- a/client.go
+++ b/client.go
@@ -432,6 +432,48 @@ func DefaultRetryPolicy(ctx context.Context, resp *http.Response, err error) (bo
 	return false, nil
 }
 
+// ErrorPropagatedRetryPolicy is the same as DefaultRetryPolicy, except it
+// propagates errors back instead of returning nil. This allows you to inspect
+// why it decided to retry or not.
+func ErrorPropagatedRetryPolicy(ctx context.Context, resp *http.Response, err error) (bool, error) {
+	// do not retry on context.Canceled or context.DeadlineExceeded
+	if ctx.Err() != nil {
+		return false, ctx.Err()
+	}
+
+	if err != nil {
+		if v, ok := err.(*url.Error); ok {
+			// Don't retry if the error was due to too many redirects.
+			if redirectsErrorRe.MatchString(v.Error()) {
+				return false, v
+			}
+
+			// Don't retry if the error was due to an invalid protocol scheme.
+			if schemeErrorRe.MatchString(v.Error()) {
+				return false, v
+			}
+
+			// Don't retry if the error was due to TLS cert verification failure.
+			if _, ok := v.Err.(x509.UnknownAuthorityError); ok {
+				return false, v
+			}
+		}
+
+		// The error is likely recoverable so retry.
+		return true, nil
+	}
+
+	// Check the response code. We retry on 500-range responses to allow
+	// the server time to recover, as 500's are typically not permanent
+	// errors and may relate to outages on the server side. This will catch
+	// invalid response codes as well, like 0 and 999.
+	if resp.StatusCode == 0 || (resp.StatusCode >= 500 && resp.StatusCode != 501) {
+		return true, fmt.Errorf("unexpected HTTP status %s", resp.Status)
+	}
+
+	return false, nil
+}
+
 // DefaultBackoff provides a default callback for Client.Backoff which
 // will perform exponential backoff based on the attempt number and limited
 // by the provided minimum and maximum durations.
@@ -509,9 +551,13 @@ func (c *Client) Do(req *Request) (*http.Response, error) {
 	}
 
 	var resp *http.Response
-	var err error
+	var attempt int
+	var shouldRetry bool
+	var doErr, checkErr error
 
 	for i := 0; ; i++ {
+		attempt++
+
 		var code int // HTTP response code
 
 		// Always rewind the request body when non-nil.
@@ -540,20 +586,20 @@ func (c *Client) Do(req *Request) (*http.Response, error) {
 		}
 
 		// Attempt the request
-		resp, err = c.HTTPClient.Do(req.Request)
+		resp, doErr = c.HTTPClient.Do(req.Request)
 		if resp != nil {
 			code = resp.StatusCode
 		}
 
 		// Check if we should continue with retries.
-		checkOK, checkErr := c.CheckRetry(req.Context(), resp, err)
+		shouldRetry, checkErr = c.CheckRetry(req.Context(), resp, doErr)
 
-		if err != nil {
+		if doErr != nil {
 			switch v := logger.(type) {
 			case Logger:
-				v.Printf("[ERR] %s %s request failed: %v", req.Method, req.URL, err)
+				v.Printf("[ERR] %s %s request failed: %v", req.Method, req.URL, doErr)
 			case LeveledLogger:
-				v.Error("request failed", "error", err, "method", req.Method, "url", req.URL)
+				v.Error("request failed", "error", doErr, "method", req.Method, "url", req.URL)
 			}
 		} else {
 			// Call this here to maintain the behavior of logging all requests,
@@ -571,13 +617,8 @@ func (c *Client) Do(req *Request) (*http.Response, error) {
 			}
 		}
 
-		// Now decide if we should continue.
-		if !checkOK {
-			if checkErr != nil {
-				err = checkErr
-			}
-			c.HTTPClient.CloseIdleConnections()
-			return resp, err
+		if !shouldRetry {
+			break
 		}
 
 		// We do this before drainBody because there's no need for the I/O if
@@ -588,7 +629,7 @@ func (c *Client) Do(req *Request) (*http.Response, error) {
 		}
 
 		// We're going to retry, consume any response to reuse the connection.
-		if err == nil && resp != nil {
+		if doErr == nil {
 			c.drainBody(resp.Body)
 		}
 
@@ -613,19 +654,37 @@ func (c *Client) Do(req *Request) (*http.Response, error) {
 		}
 	}
 
+	// this is the closest we have to success criteria
+	if doErr == nil && checkErr == nil && !shouldRetry {
+		return resp, nil
+	}
+
+	defer c.HTTPClient.CloseIdleConnections()
+
+	err := doErr
+	if checkErr != nil {
+		err = checkErr
+	}
+
 	if c.ErrorHandler != nil {
-		c.HTTPClient.CloseIdleConnections()
-		return c.ErrorHandler(resp, err, c.RetryMax+1)
+		return c.ErrorHandler(resp, err, attempt)
 	}
 
 	// By default, we close the response body and return an error without
 	// returning the response
 	if resp != nil {
-		resp.Body.Close()
+		c.drainBody(resp.Body)
 	}
-	c.HTTPClient.CloseIdleConnections()
-	return nil, fmt.Errorf("%s %s giving up after %d attempts",
-		req.Method, req.URL, c.RetryMax+1)
+
+	// this means CheckRetry thought the request was a failure, but didn't
+	// communicate why
+	if err == nil {
+		return nil, fmt.Errorf("%s %s giving up after %d attempt(s)",
+			req.Method, req.URL, attempt)
+	}
+
+	return nil, fmt.Errorf("%s %s giving up after %d attempt(s): %w",
+		req.Method, req.URL, attempt, err)
 }
 
 // Try to read the response body so we can reuse this connection.
diff --git a/client_test.go b/client_test.go
index dcacb01..27442e0 100644
--- a/client_test.go
+++ b/client_test.go
@@ -4,6 +4,7 @@ import (
 	"bytes"
 	"context"
 	"errors"
+	"fmt"
 	"io"
 	"io/ioutil"
 	"net"
@@ -255,22 +256,44 @@ func TestClient_Do_fails(t *testing.T) {
 	}))
 	defer ts.Close()
 
-	// Create the client. Use short retry windows so we fail faster.
-	client := NewClient()
-	client.RetryWaitMin = 10 * time.Millisecond
-	client.RetryWaitMax = 10 * time.Millisecond
-	client.RetryMax = 2
-
-	// Create the request
-	req, err := NewRequest("POST", ts.URL, nil)
-	if err != nil {
-		t.Fatalf("err: %v", err)
+	tests := []struct {
+		name string
+		cr   CheckRetry
+		err  string
+	}{
+		{
+			name: "default_retry_policy",
+			cr:   DefaultRetryPolicy,
+			err:  "giving up after 3 attempt(s)",
+		},
+		{
+			name: "error_propagated_retry_policy",
+			cr:   ErrorPropagatedRetryPolicy,
+			err:  "giving up after 3 attempt(s): unexpected HTTP status 500 Internal Server Error",
+		},
 	}
 
-	// Send the request.
-	_, err = client.Do(req)
-	if err == nil || !strings.Contains(err.Error(), "giving up") {
-		t.Fatalf("expected giving up error, got: %#v", err)
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			// Create the client. Use short retry windows so we fail faster.
+			client := NewClient()
+			client.RetryWaitMin = 10 * time.Millisecond
+			client.RetryWaitMax = 10 * time.Millisecond
+			client.CheckRetry = tt.cr
+			client.RetryMax = 2
+
+			// Create the request
+			req, err := NewRequest("POST", ts.URL, nil)
+			if err != nil {
+				t.Fatalf("err: %v", err)
+			}
+
+			// Send the request.
+			_, err = client.Do(req)
+			if err == nil || !strings.HasSuffix(err.Error(), tt.err) {
+				t.Fatalf("expected giving up error, got: %#v", err)
+			}
+		})
 	}
 }
 
@@ -462,8 +485,10 @@ func TestClient_RequestWithContext(t *testing.T) {
 		t.Fatalf("CheckRetry called %d times, expected 1", called)
 	}
 
-	if err != context.Canceled {
-		t.Fatalf("Expected context.Canceled err, got: %v", err)
+	e := fmt.Sprintf("GET %s giving up after 1 attempt(s): %s", ts.URL, context.Canceled.Error())
+
+	if err.Error() != e {
+		t.Fatalf("Expected err to contain %s, got: %v", e, err)
 	}
 }
 
@@ -493,10 +518,9 @@ func TestClient_CheckRetry(t *testing.T) {
 		t.Fatalf("CheckRetry called %d times, expected 1", called)
 	}
 
-	if err != retryErr {
+	if err.Error() != fmt.Sprintf("GET %s giving up after 2 attempt(s): retryError", ts.URL) {
 		t.Fatalf("Expected retryError, got:%v", err)
 	}
-
 }
 
 func TestClient_DefaultRetryPolicy_TLS(t *testing.T) {