diff --git a/client.go b/client.go
index efee53c..1423605 100644
--- a/client.go
+++ b/client.go
@@ -687,6 +687,14 @@ func (c *Client) Do(req *Request) (*http.Response, error) {
 			}
 		}
 
+		// First attempt was already signed
+		if attempt > 1 && c.PrepareRetry != nil {
+			if err := c.PrepareRetry(req.Request); err != nil {
+				prepareErr = err
+				break
+			}
+		}
+
 		if c.RequestLogHook != nil {
 			switch v := logger.(type) {
 			case LeveledLogger:
@@ -778,12 +786,6 @@ func (c *Client) Do(req *Request) (*http.Response, error) {
 		httpreq := *req.Request
 		req.Request = &httpreq
 
-		if c.PrepareRetry != nil {
-			if err := c.PrepareRetry(req.Request); err != nil {
-				prepareErr = err
-				break
-			}
-		}
 	}
 
 	// this is the closest we have to success criteria
diff --git a/client_test.go b/client_test.go
index cc05e91..1c320fe 100644
--- a/client_test.go
+++ b/client_test.go
@@ -6,6 +6,8 @@ package retryablehttp
 import (
 	"bytes"
 	"context"
+	"crypto/sha256"
+	"encoding/base64"
 	"errors"
 	"fmt"
 	"io"
@@ -372,6 +374,21 @@ func TestClient_Do_WithPrepareRetry(t *testing.T) {
 	client.PrepareRetry = func(req *http.Request) error {
 		prepareChecks++
 		req.Header.Set("foo", strconv.Itoa(prepareChecks))
+
+		// if the method is POST or PUT, set a header based on request body content
+		if req.Method == "POST" || req.Method == "PUT" {
+			bodyBytes, err := io.ReadAll(req.Body)
+			if err != nil {
+				t.Fatalf("could not read request body: %s", err)
+			}
+			preparedBody := string(bodyBytes)
+
+			if len(preparedBody) > 0 {
+				sum := sha256.Sum256([]byte(preparedBody))
+				contentHash := base64.StdEncoding.EncodeToString(sum[:])
+				req.Header.Set("content_hash", contentHash)
+			}
+		}
 		return nil
 	}
 
@@ -384,6 +401,8 @@ func TestClient_Do_WithPrepareRetry(t *testing.T) {
 	var shouldSucceed bool
 	tests := []struct {
 		name                  string
+		method                string
+		requestBody           string
 		handler               ResponseHandlerFunc
 		expectedChecks        int // often 2x number of attempts since we check twice
 		expectedPrepareChecks int
@@ -391,12 +410,14 @@ func TestClient_Do_WithPrepareRetry(t *testing.T) {
 	}{
 		{
 			name:                  "nil handler",
+			method:                http.MethodGet,
 			handler:               nil,
 			expectedChecks:        1,
 			expectedPrepareChecks: 0,
 		},
 		{
-			name: "handler always succeeds",
+			name:   "handler always succeeds",
+			method: http.MethodGet,
 			handler: func(*http.Response) error {
 				return nil
 			},
@@ -404,7 +425,8 @@ func TestClient_Do_WithPrepareRetry(t *testing.T) {
 			expectedPrepareChecks: 0,
 		},
 		{
-			name: "handler always fails in a retryable way",
+			name:   "handler always fails in a retryable way",
+			method: http.MethodGet,
 			handler: func(*http.Response) error {
 				return errors.New("retryable failure")
 			},
@@ -412,7 +434,8 @@ func TestClient_Do_WithPrepareRetry(t *testing.T) {
 			expectedPrepareChecks: 2,
 		},
 		{
-			name: "handler always fails in a nonretryable way",
+			name:   "handler always fails in a nonretryable way",
+			method: http.MethodGet,
 			handler: func(*http.Response) error {
 				return errors.New("nonretryable failure")
 			},
@@ -420,7 +443,8 @@ func TestClient_Do_WithPrepareRetry(t *testing.T) {
 			expectedPrepareChecks: 0,
 		},
 		{
-			name: "handler succeeds on second attempt",
+			name:   "handler succeeds on second attempt",
+			method: http.MethodGet,
 			handler: func(*http.Response) error {
 				if shouldSucceed {
 					return nil
@@ -431,6 +455,34 @@ func TestClient_Do_WithPrepareRetry(t *testing.T) {
 			expectedChecks:        4,
 			expectedPrepareChecks: 1,
 		},
+		{
+			name:        "POST - handler succeeds on second attempt, using body for PrepareRetry",
+			method:      http.MethodPost,
+			requestBody: "dummy data",
+			handler: func(response *http.Response) error {
+				if shouldSucceed {
+					return nil
+				}
+				shouldSucceed = true
+				return errors.New("retryable failure")
+			},
+			expectedChecks:        4,
+			expectedPrepareChecks: 1,
+		},
+		{
+			name:        "PUT - handler succeeds on second attempt, using body for PrepareRetry",
+			method:      http.MethodPut,
+			requestBody: "dummy data",
+			handler: func(response *http.Response) error {
+				if shouldSucceed {
+					return nil
+				}
+				shouldSucceed = true
+				return errors.New("retryable failure")
+			},
+			expectedChecks:        4,
+			expectedPrepareChecks: 1,
+		},
 	}
 
 	for _, tt := range tests {
@@ -438,8 +490,16 @@ func TestClient_Do_WithPrepareRetry(t *testing.T) {
 			checks = 0
 			prepareChecks = 0
 			shouldSucceed = false
+			var req *Request
+			var err error
+
 			// Create the request
-			req, err := NewRequest("GET", ts.URL, nil)
+			if tt.requestBody != "" {
+				req, err = NewRequest(tt.method, ts.URL, strings.NewReader(tt.requestBody))
+			} else {
+				req, err = NewRequest(tt.method, ts.URL, nil)
+			}
+
 			if err != nil {
 				t.Fatalf("err: %v", err)
 			}
@@ -470,6 +530,12 @@ func TestClient_Do_WithPrepareRetry(t *testing.T) {
 				t.Fatalf("expected changes in request header 'foo' '%s', but got '%s'", expectedHeader, header)
 			}
 
+			if tt.method == "POST" || tt.method == "PUT" {
+				headerFromContent := req.Request.Header.Get("content_hash")
+				if headerFromContent == "" {
+					t.Fatalf("expected 'content_hash' header to exist, but it does not")
+				}
+			}
 		})
 	}
 }