diff --git a/appsTransport.go b/appsTransport.go
index ada64bc..4852d83 100644
--- a/appsTransport.go
+++ b/appsTransport.go
@@ -24,7 +24,7 @@ type AppsTransport struct {
 	BaseURL string            // BaseURL is the scheme and host for GitHub API, defaults to https://api.github.com
 	Client  Client            // Client to use to refresh tokens, defaults to http.Client with provided transport
 	tr      http.RoundTripper // tr is the underlying roundtripper being wrapped
-	signer  Signer            // signer signs JWT tokens.
+	signer  SignerWithContext // signer signs JWT tokens.
 	appID   int64             // appID is the GitHub App's ID
 }
 
@@ -94,7 +94,7 @@ func (t *AppsTransport) RoundTrip(req *http.Request) (*http.Response, error) {
 		Issuer:    strconv.FormatInt(t.appID, 10),
 	}
 
-	ss, err := t.signer.Sign(claims)
+	ss, err := t.signer.SignContext(req.Context(), claims)
 	if err != nil {
 		return nil, fmt.Errorf("could not sign jwt: %s", err)
 	}
@@ -113,8 +113,19 @@ func (t *AppsTransport) AppID() int64 {
 
 type AppsTransportOption func(*AppsTransport)
 
-// WithSigner configures the AppsTransport to use the given Signer for generating JWT tokens.
+// WithSigner configures the AppsTransport to use the given Signer for
+// generating JWT tokens.
+//
+// Deprecated: Use [WithContextSigner] instead.
 func WithSigner(signer Signer) AppsTransportOption {
+	return func(at *AppsTransport) {
+		at.signer = SignerWithContextAdapter{signer}
+	}
+}
+
+// WithContextSigner configures the AppsTransport to use the given Signer for
+// generating JWT tokens.
+func WithContextSigner(signer SignerWithContext) AppsTransportOption {
 	return func(at *AppsTransport) {
 		at.signer = signer
 	}
diff --git a/appsTransport_test.go b/appsTransport_test.go
index 37a2b2c..3f5092e 100644
--- a/appsTransport_test.go
+++ b/appsTransport_test.go
@@ -2,6 +2,7 @@ package ghinstallation
 
 import (
 	"bytes"
+	"context"
 	"fmt"
 	"net/http"
 	"net/http/httptest"
@@ -110,33 +111,76 @@ func TestJWTExpiry(t *testing.T) {
 }
 
 func TestCustomSigner(t *testing.T) {
-	check := RoundTrip{
-		rt: func(req *http.Request) (*http.Response, error) {
-			h, ok := req.Header["Authorization"]
-			if !ok {
-				t.Error("Header Accept not set")
-			}
-			want := []string{"Bearer hunter2"}
-			if diff := cmp.Diff(want, h); diff != "" {
-				t.Errorf("HTTP Accept headers want->got: %s", diff)
-			}
-			return nil, nil
+	tc := []struct {
+		nm           string
+		option       AppsTransportOption
+		bearerSuffix string
+	}{
+		{
+			nm:           "context-free signer",
+			option:       WithSigner(&noopSigner{}),
+			bearerSuffix: "",
+		},
+		{
+			nm:           "context signer",
+			option:       WithContextSigner(&noopSigner{}),
+			bearerSuffix: ":context",
 		},
 	}
 
-	tr, err := NewAppsTransportWithOptions(check, appID, WithSigner(&noopSigner{}))
-	if err != nil {
-		t.Fatalf("NewAppsTransportWithOptions: %v", err)
-	}
+	for _, c := range tc {
+		t.Run(c.nm, func(t *testing.T) {
+			check := AuthCaptureRoundTripper{}
 
-	req := httptest.NewRequest(http.MethodGet, "http://example.com", new(bytes.Buffer))
-	if _, err := tr.RoundTrip(req); err != nil {
-		t.Fatalf("error calling RoundTrip: %v", err)
+			tr, err := NewAppsTransportWithOptions(&check, appID, c.option)
+			if err != nil {
+				t.Fatalf("NewAppsTransportWithOptions: %v", err)
+			}
+
+			req := httptest.NewRequest(http.MethodGet, "http://example.com", new(bytes.Buffer))
+			req = req.WithContext(
+				context.WithValue(context.Background(), contextSignerKey(struct{}{}), c.bearerSuffix),
+			)
+
+			if _, err := tr.RoundTrip(req); err != nil {
+				t.Fatalf("error calling RoundTrip: %v", err)
+			}
+
+			if !check.Captured {
+				t.Error("Header Authorization not set")
+			}
+
+			want := []string{"Bearer hunter2" + c.bearerSuffix}
+			if diff := cmp.Diff(want, check.Value); diff != "" {
+				t.Errorf("HTTP Authorization header want->got: %s", diff)
+			}
+		})
 	}
 }
 
+type contextSignerKey struct{}
+
 type noopSigner struct{}
 
 func (noopSigner) Sign(jwt.Claims) (string, error) {
 	return "hunter2", nil
 }
+
+func (noopSigner) SignContext(ctx context.Context, _ jwt.Claims) (string, error) {
+	// mark the returned token with the context suffix expected by the test
+	v := ctx.Value(contextSignerKey(struct{}{}))
+	return fmt.Sprintf("hunter2%v", v), nil
+}
+
+type AuthCaptureRoundTripper struct {
+	Captured bool
+	Value    []string
+}
+
+func (a *AuthCaptureRoundTripper) RoundTrip(req *http.Request) (*http.Response, error) {
+	h, ok := req.Header["Authorization"]
+	a.Captured = ok
+	a.Value = h
+
+	return nil, nil
+}
diff --git a/sign.go b/sign.go
index 928e10e..1039ec6 100644
--- a/sign.go
+++ b/sign.go
@@ -1,19 +1,39 @@
 package ghinstallation
 
 import (
+	"context"
 	"crypto/rsa"
 
 	jwt "github.com/golang-jwt/jwt/v4"
 )
 
-// Signer is a JWT token signer. This is a wrapper around [jwt.SigningMethod] with predetermined
-// key material.
+// Signer is a JWT token signer. This is a wrapper around [jwt.SigningMethod]
+// with predetermined key material.
 type Signer interface {
 	// Sign signs the given claims and returns a JWT token string, as specified
 	// by [jwt.Token.SignedString]
 	Sign(claims jwt.Claims) (string, error)
 }
 
+// SignerWithContext is a JWT token signer. This is a wrapper around
+// [jwt.SigningMethod] with predetermined key material.
+type SignerWithContext interface {
+	// SignContext signs the given claims and returns a JWT token string, as
+	// specified by [jwt.Token.SignedString]. The signing operation should use the
+	// provided context as appropriate.
+	SignContext(ctx context.Context, claims jwt.Claims) (string, error)
+}
+
+// SignerWithContextAdapter is a simple [Signer] wrapper that allows it to act
+// as a [SignerWithContext].
+type SignerWithContextAdapter struct {
+	Signer Signer
+}
+
+func (s SignerWithContextAdapter) SignContext(_ context.Context, claims jwt.Claims) (string, error) {
+	return s.Signer.Sign(claims)
+}
+
 // RSASigner signs JWT tokens using RSA keys.
 type RSASigner struct {
 	method *jwt.SigningMethodRSA
@@ -28,6 +48,13 @@ func NewRSASigner(method *jwt.SigningMethodRSA, key *rsa.PrivateKey) *RSASigner
 }
 
 // Sign signs the JWT claims with the RSA key.
+//
+// Deprecated: Use [SignContext] instead.
 func (s *RSASigner) Sign(claims jwt.Claims) (string, error) {
 	return jwt.NewWithClaims(s.method, claims).SignedString(s.key)
 }
+
+// Sign signs the JWT claims with the RSA key.
+func (s *RSASigner) SignContext(_ context.Context, claims jwt.Claims) (string, error) {
+	return s.Sign(claims)
+}