diff --git a/auth.go b/auth.go
index 7579b4a..9c473a1 100644
--- a/auth.go
+++ b/auth.go
@@ -3,6 +3,7 @@ package reggie
 import (
 	"encoding/json"
 	"errors"
+	"fmt"
 	"regexp"
 	"strings"
 
@@ -36,6 +37,13 @@ func (client *Client) retryRequestWithAuth(originalRequest *Request, originalRes
 		originalRequest.QueryParam.Del(k)
 	}
 
+	if originalRequest.retryCallback != nil {
+		err := originalRequest.retryCallback(originalRequest)
+		if err != nil {
+			return nil, fmt.Errorf("retry callback returned error: %s", err)
+		}
+	}
+
 	authenticationType := authHeaderMatcher.ReplaceAllString(authHeaderRaw, "$1")
 	if strings.EqualFold(authenticationType, "bearer") {
 		h := parseAuthHeader(authHeaderRaw)
diff --git a/client.go b/client.go
index 85bf4de..4514bcd 100644
--- a/client.go
+++ b/client.go
@@ -133,7 +133,10 @@ func (client *Client) NewRequest(method string, path string, opts ...requestOpti
 	restyRequest.URL = url
 	restyRequest.SetHeader("User-Agent", client.Config.UserAgent)
 
-	return &Request{restyRequest}
+	return &Request{
+		Request:       restyRequest,
+		retryCallback: r.RetryCallback,
+	}
 }
 
 // Do executes a Request and returns a Response.
diff --git a/client_test.go b/client_test.go
index e51d9e2..4ac26df 100644
--- a/client_test.go
+++ b/client_test.go
@@ -3,6 +3,7 @@ package reggie
 import (
 	"bytes"
 	"encoding/base64"
+	"errors"
 	"fmt"
 	"net/http"
 	"net/http/httptest"
@@ -260,6 +261,34 @@ func TestClient(t *testing.T) {
 		t.Fatalf("Expected body to be \"abc\" but instead got %s", lastCapturedRequestBodyStr)
 	}
 
+	// Test that the retry callback is invoked, if configured.
+	newBody := "not the original body"
+	req = client.NewRequest(PUT, "/a/b/c", WithRetryCallback(func(r *Request) error {
+		r.SetBody(newBody)
+		return nil
+	})).SetBody([]byte("original body"))
+	_, err = client.Do(req)
+	if err != nil {
+		t.Fatalf("Errors executing request: %s", err)
+	}
+
+	// Ensure the request ended up with the new body.
+	if lastCapturedRequestBodyStr != newBody {
+		t.Fatalf("Expected body to be %q, but instead got %q", newBody, lastCapturedRequestBodyStr)
+	}
+
+	// Test the case where the retry callback returns an error.
+	req = client.NewRequest(PUT, "/a/b/c", WithRetryCallback(func(r *Request) error {
+		return errors.New("uh oh")
+	})).SetBody([]byte("original body"))
+	_, err = client.Do(req)
+	if err == nil {
+		t.Fatalf("Expected error from callback function, but request returned no error")
+	}
+	if !strings.Contains(err.Error(), "uh oh") {
+		t.Fatalf("Expected error to contain callback error \"uh oh\", but instead got %q", err)
+	}
+
 	// test for access_token vs. token
 	authUseAccessToken = true
 	req = client.NewRequest(GET, "/v2/<name>/tags/list")
diff --git a/request.go b/request.go
index 45425da..6be5ae0 100644
--- a/request.go
+++ b/request.go
@@ -8,16 +8,22 @@ import (
 )
 
 type (
+	// RetryCallbackFunc is a function that can mutate a request prior to it
+	// being retried.
+	RetryCallbackFunc func(*Request) error
+
 	// Request is an HTTP request to be sent to an OCI registry.
 	Request struct {
 		*resty.Request
+		retryCallback RetryCallbackFunc
 	}
 
 	requestConfig struct {
-		Name      string
-		Reference string
-		Digest    string
-		SessionID string
+		Name          string
+		Reference     string
+		Digest        string
+		SessionID     string
+		RetryCallback RetryCallbackFunc
 	}
 
 	requestOption func(c *requestConfig)
@@ -51,6 +57,15 @@ func WithSessionID(id string) requestOption {
 	}
 }
 
+// WithRetryCallback specifies a callback that will be invoked before a request
+// is retried. This is useful for, e.g., ensuring an io.Reader used for the body
+// will produce the right content on retry.
+func WithRetryCallback(cb RetryCallbackFunc) requestOption {
+	return func(c *requestConfig) {
+		c.RetryCallback = cb
+	}
+}
+
 // SetBody wraps the resty SetBody and returns the request, allowing method chaining
 func (req *Request) SetBody(body interface{}) *Request {
 	req.Request.SetBody(body)