diff --git a/.chloggen/grpc-extension-context.yaml b/.chloggen/grpc-extension-context.yaml
new file mode 100644
index 00000000000..652a3b2381b
--- /dev/null
+++ b/.chloggen/grpc-extension-context.yaml
@@ -0,0 +1,11 @@
+change_type: bug_fix
+
+component: pkg/extensionmiddleware
+
+note: Add context.Context to gRPC middleware interface constructors. 
+
+subtext: This is a breaking API change for components that implement or use extensionmiddleware.
+
+issues: [14523]
+
+change_logs: [api]
diff --git a/.chloggen/grpc-middlware-context.yaml b/.chloggen/grpc-middlware-context.yaml
new file mode 100644
index 00000000000..e0972c8894e
--- /dev/null
+++ b/.chloggen/grpc-middlware-context.yaml
@@ -0,0 +1,9 @@
+change_type: bug_fix
+
+component: pkg/config/configmiddleware
+
+note: Add context.Context to gRPC middleware interface constructors. 
+
+issues: [14523]
+
+change_logs: [api]
diff --git a/config/configgrpc/client_middleware_test.go b/config/configgrpc/client_middleware_test.go
index 7ddb99ba164..58fedd60900 100644
--- a/config/configgrpc/client_middleware_test.go
+++ b/config/configgrpc/client_middleware_test.go
@@ -40,7 +40,7 @@ func newTestMiddlewareConfig(name string) configmiddleware.Config {
 func newTestClientMiddleware(name string) extension.Extension {
 	return &testClientMiddleware{
 		Extension: extensionmiddlewaretest.NewNop(),
-		GetGRPCClientOptionsFunc: func() ([]grpc.DialOption, error) {
+		GetGRPCClientOptionsFunc: func(_ context.Context) ([]grpc.DialOption, error) {
 			return []grpc.DialOption{
 				grpc.WithChainUnaryInterceptor(
 					func(
diff --git a/config/configgrpc/server_middleware_test.go b/config/configgrpc/server_middleware_test.go
index c62748c78be..3512445fa49 100644
--- a/config/configgrpc/server_middleware_test.go
+++ b/config/configgrpc/server_middleware_test.go
@@ -46,7 +46,7 @@ type testServerMiddleware struct {
 func newTestServerMiddleware(name string) extension.Extension {
 	return &testServerMiddleware{
 		Extension: extensionmiddlewaretest.NewNop(),
-		GetGRPCServerOptionsFunc: func() ([]grpc.ServerOption, error) {
+		GetGRPCServerOptionsFunc: func(_ context.Context) ([]grpc.ServerOption, error) {
 			return []grpc.ServerOption{grpc.ChainUnaryInterceptor(
 				func(
 					ctx context.Context,
diff --git a/config/configmiddleware/configmiddleware.go b/config/configmiddleware/configmiddleware.go
index 831ba7766fe..a41f46af8dc 100644
--- a/config/configmiddleware/configmiddleware.go
+++ b/config/configmiddleware/configmiddleware.go
@@ -68,10 +68,10 @@ func (m Config) GetHTTPServerHandler(_ context.Context, extensions map[component
 // extensionmiddleware.GRPCClient from the map of extensions, and
 // returns the gRPC dial options. If a middleware is not found, an
 // error is returned.  This should only be used by gRPC clients.
-func (m Config) GetGRPCClientOptions(_ context.Context, extensions map[component.ID]component.Component) ([]grpc.DialOption, error) {
+func (m Config) GetGRPCClientOptions(ctx context.Context, extensions map[component.ID]component.Component) ([]grpc.DialOption, error) {
 	if ext, found := extensions[m.ID]; found {
 		if client, ok := ext.(extensionmiddleware.GRPCClient); ok {
-			return client.GetGRPCClientOptions()
+			return client.GetGRPCClientOptions(ctx)
 		}
 		return nil, errNotGRPCClient
 	}
@@ -82,10 +82,10 @@ func (m Config) GetGRPCClientOptions(_ context.Context, extensions map[component
 // extensionmiddleware.GRPCServer from the map of extensions, and
 // returns the gRPC server options. If a middleware is not found, an
 // error is returned.  This should only be used by gRPC servers.
-func (m Config) GetGRPCServerOptions(_ context.Context, extensions map[component.ID]component.Component) ([]grpc.ServerOption, error) {
+func (m Config) GetGRPCServerOptions(ctx context.Context, extensions map[component.ID]component.Component) ([]grpc.ServerOption, error) {
 	if ext, found := extensions[m.ID]; found {
 		if server, ok := ext.(extensionmiddleware.GRPCServer); ok {
-			return server.GetGRPCServerOptions()
+			return server.GetGRPCServerOptions(ctx)
 		}
 		return nil, errNotGRPCServer
 	}
diff --git a/config/configmiddleware/configmiddleware_test.go b/config/configmiddleware/configmiddleware_test.go
index 5cdb2628fba..7551f5346ec 100644
--- a/config/configmiddleware/configmiddleware_test.go
+++ b/config/configmiddleware/configmiddleware_test.go
@@ -149,7 +149,7 @@ func TestConfig_GetGRPCServerOptions(t *testing.T) {
 					extensionmiddleware.GetGRPCServerOptionsFunc
 				}{
 					Extension: extensionmiddlewaretest.NewNop(),
-					GetGRPCServerOptionsFunc: func() ([]grpc.ServerOption, error) {
+					GetGRPCServerOptionsFunc: func(context.Context) ([]grpc.ServerOption, error) {
 						return []grpc.ServerOption{
 							grpc.EmptyServerOption{},
 						}, nil
@@ -212,7 +212,7 @@ func TestConfig_GetGRPCClientOptions(t *testing.T) {
 					extensionmiddleware.GetGRPCClientOptionsFunc
 				}{
 					Extension: extensionmiddlewaretest.NewNop(),
-					GetGRPCClientOptionsFunc: func() ([]grpc.DialOption, error) {
+					GetGRPCClientOptionsFunc: func(_ context.Context) ([]grpc.DialOption, error) {
 						return []grpc.DialOption{
 							grpc.EmptyDialOption{},
 						}, nil
diff --git a/extension/extensionmiddleware/client.go b/extension/extensionmiddleware/client.go
index fb24a18339e..547c74b4486 100644
--- a/extension/extensionmiddleware/client.go
+++ b/extension/extensionmiddleware/client.go
@@ -4,6 +4,7 @@
 package extensionmiddleware // import "go.opentelemetry.io/collector/extension/extensionmiddleware"
 
 import (
+	"context"
 	"net/http"
 
 	"google.golang.org/grpc"
@@ -18,7 +19,7 @@ type HTTPClient interface {
 // GRPCClient is an interface for gRPC client middleware extensions.
 type GRPCClient interface {
 	// GetGRPCClientOptions returns the gRPC dial options to use for client connections.
-	GetGRPCClientOptions() ([]grpc.DialOption, error)
+	GetGRPCClientOptions(context.Context) ([]grpc.DialOption, error)
 }
 
 var _ HTTPClient = (*GetHTTPRoundTripperFunc)(nil)
@@ -36,11 +37,11 @@ func (f GetHTTPRoundTripperFunc) GetHTTPRoundTripper(base http.RoundTripper) (ht
 var _ GRPCClient = (*GetGRPCClientOptionsFunc)(nil)
 
 // GetGRPCClientOptionsFunc is a function that implements GRPCClient.
-type GetGRPCClientOptionsFunc func() ([]grpc.DialOption, error)
+type GetGRPCClientOptionsFunc func(context.Context) ([]grpc.DialOption, error)
 
-func (f GetGRPCClientOptionsFunc) GetGRPCClientOptions() ([]grpc.DialOption, error) {
+func (f GetGRPCClientOptionsFunc) GetGRPCClientOptions(ctx context.Context) ([]grpc.DialOption, error) {
 	if f == nil {
 		return nil, nil
 	}
-	return f()
+	return f(ctx)
 }
diff --git a/extension/extensionmiddleware/client_test.go b/extension/extensionmiddleware/client_test.go
index 8d4eadcade2..9161e6236f7 100644
--- a/extension/extensionmiddleware/client_test.go
+++ b/extension/extensionmiddleware/client_test.go
@@ -4,6 +4,7 @@
 package extensionmiddleware
 
 import (
+	"context"
 	"errors"
 	"net/http"
 	"testing"
@@ -46,44 +47,42 @@ func TestGetHTTPRoundTripperFunc(t *testing.T) {
 }
 
 func TestGetGRPCClientOptionsFunc(t *testing.T) {
+	type testCtx struct{}
+	var (
+		key   = testCtx{}
+		value = "testval"
+	)
+	testctx := context.WithValue(context.Background(), key, value)
+
 	t.Run("nil function", func(t *testing.T) {
 		var nilFunc GetGRPCClientOptionsFunc
-		options, err := nilFunc.GetGRPCClientOptions()
+		options, err := nilFunc.GetGRPCClientOptions(testctx)
 		require.NoError(t, err)
 		require.Nil(t, options)
 	})
 
-	t.Run("empty options function", func(t *testing.T) {
-		emptyFunc := GetGRPCClientOptionsFunc(func() ([]grpc.DialOption, error) {
-			return []grpc.DialOption{}, nil
-		})
-
-		options, err := emptyFunc.GetGRPCClientOptions()
-		require.NoError(t, err)
-		require.Empty(t, options)
-	})
-
 	t.Run("options function", func(t *testing.T) {
-		// Create some test dial options
 		dialOpt1 := grpc.WithAuthority("test-authority")
 		dialOpt2 := grpc.WithDisableRetry()
 
-		optionsFunc := GetGRPCClientOptionsFunc(func() ([]grpc.DialOption, error) {
+		optionsFunc := GetGRPCClientOptionsFunc(func(ctx context.Context) ([]grpc.DialOption, error) {
+			require.Equal(t, ctx.Value(key), value)
 			return []grpc.DialOption{dialOpt1, dialOpt2}, nil
 		})
 
-		options, err := optionsFunc.GetGRPCClientOptions()
+		options, err := optionsFunc.GetGRPCClientOptions(testctx)
 		require.NoError(t, err)
 		require.Len(t, options, 2)
 	})
 
 	t.Run("error function", func(t *testing.T) {
 		expectedErr := errors.New("grpc options error")
-		errorFunc := GetGRPCClientOptionsFunc(func() ([]grpc.DialOption, error) {
+		errorFunc := GetGRPCClientOptionsFunc(func(ctx context.Context) ([]grpc.DialOption, error) {
+			require.Equal(t, ctx.Value(key), value)
 			return nil, expectedErr
 		})
 
-		options, err := errorFunc.GetGRPCClientOptions()
+		options, err := errorFunc.GetGRPCClientOptions(testctx)
 		require.Error(t, err)
 		require.Equal(t, expectedErr, err)
 		require.Nil(t, options)
diff --git a/extension/extensionmiddleware/extensionmiddlewaretest/err.go b/extension/extensionmiddleware/extensionmiddlewaretest/err.go
index b881dae2c51..262c82d0f03 100644
--- a/extension/extensionmiddleware/extensionmiddlewaretest/err.go
+++ b/extension/extensionmiddleware/extensionmiddlewaretest/err.go
@@ -4,6 +4,7 @@
 package extensionmiddlewaretest // import "go.opentelemetry.io/collector/extension/extensionmiddleware/extensionmiddlewaretest"
 
 import (
+	"context"
 	"net/http"
 
 	"google.golang.org/grpc"
@@ -37,13 +38,13 @@ func NewErr(err error) extension.Extension {
 		GetHTTPRoundTripperFunc: func(http.RoundTripper) (http.RoundTripper, error) {
 			return nil, err
 		},
-		GetGRPCClientOptionsFunc: func() ([]grpc.DialOption, error) {
+		GetGRPCClientOptionsFunc: func(context.Context) ([]grpc.DialOption, error) {
 			return nil, err
 		},
 		GetHTTPHandlerFunc: func(http.Handler) (http.Handler, error) {
 			return nil, err
 		},
-		GetGRPCServerOptionsFunc: func() ([]grpc.ServerOption, error) {
+		GetGRPCServerOptionsFunc: func(context.Context) ([]grpc.ServerOption, error) {
 			return nil, err
 		},
 	}
diff --git a/extension/extensionmiddleware/extensionmiddlewaretest/err_test.go b/extension/extensionmiddleware/extensionmiddlewaretest/err_test.go
index 14bcf291b5b..0ebbbf3ba64 100644
--- a/extension/extensionmiddleware/extensionmiddlewaretest/err_test.go
+++ b/extension/extensionmiddleware/extensionmiddlewaretest/err_test.go
@@ -4,6 +4,7 @@
 package extensionmiddlewaretest
 
 import (
+	"context"
 	"errors"
 	"testing"
 
@@ -22,7 +23,7 @@ func TestErrClient(t *testing.T) {
 
 	grpcClient, ok := client.(extensionmiddleware.GRPCClient)
 	require.True(t, ok)
-	_, err = grpcClient.GetGRPCClientOptions()
+	_, err = grpcClient.GetGRPCClientOptions(context.Background())
 	require.Error(t, err)
 }
 
@@ -36,6 +37,6 @@ func TestErrServer(t *testing.T) {
 
 	grpcServer, ok := server.(extensionmiddleware.GRPCServer)
 	require.True(t, ok)
-	_, err = grpcServer.GetGRPCServerOptions()
+	_, err = grpcServer.GetGRPCServerOptions(context.Background())
 	require.Error(t, err)
 }
diff --git a/extension/extensionmiddleware/extensionmiddlewaretest/nop_test.go b/extension/extensionmiddleware/extensionmiddlewaretest/nop_test.go
index d1190fbff98..6146ee7eceb 100644
--- a/extension/extensionmiddleware/extensionmiddlewaretest/nop_test.go
+++ b/extension/extensionmiddleware/extensionmiddlewaretest/nop_test.go
@@ -4,6 +4,7 @@
 package extensionmiddlewaretest
 
 import (
+	"context"
 	"net/http"
 	"testing"
 
@@ -23,7 +24,7 @@ func TestNopClient(t *testing.T) {
 
 	grpcClient, ok := client.(extensionmiddleware.GRPCClient)
 	require.True(t, ok)
-	grpcOpts, err := grpcClient.GetGRPCClientOptions()
+	grpcOpts, err := grpcClient.GetGRPCClientOptions(context.Background())
 	require.NoError(t, err)
 	require.Nil(t, grpcOpts)
 }
@@ -39,7 +40,7 @@ func TestNopServer(t *testing.T) {
 
 	grpcServer, ok := client.(extensionmiddleware.GRPCServer)
 	require.True(t, ok)
-	grpcOpts, err := grpcServer.GetGRPCServerOptions()
+	grpcOpts, err := grpcServer.GetGRPCServerOptions(context.Background())
 	require.NoError(t, err)
 	require.Nil(t, grpcOpts)
 }
diff --git a/extension/extensionmiddleware/server.go b/extension/extensionmiddleware/server.go
index 6fa9ca1ae60..6cb280eb7ea 100644
--- a/extension/extensionmiddleware/server.go
+++ b/extension/extensionmiddleware/server.go
@@ -4,6 +4,7 @@
 package extensionmiddleware // import "go.opentelemetry.io/collector/extension/extensionmiddleware"
 
 import (
+	"context"
 	"net/http"
 
 	"google.golang.org/grpc"
@@ -18,7 +19,7 @@ type HTTPServer interface {
 // GRPCServer defines the interface for gRPC server middleware extensions.
 type GRPCServer interface {
 	// GetGRPCServerOptions returns options for a gRPC server.
-	GetGRPCServerOptions() ([]grpc.ServerOption, error)
+	GetGRPCServerOptions(context.Context) ([]grpc.ServerOption, error)
 }
 
 var _ HTTPServer = (*GetHTTPHandlerFunc)(nil)
@@ -36,11 +37,11 @@ func (f GetHTTPHandlerFunc) GetHTTPHandler(base http.Handler) (http.Handler, err
 var _ GRPCServer = (*GetGRPCServerOptionsFunc)(nil)
 
 // GetGRPCServerOptionsFunc is a function that implements GRPCServer.
-type GetGRPCServerOptionsFunc func() ([]grpc.ServerOption, error)
+type GetGRPCServerOptionsFunc func(context.Context) ([]grpc.ServerOption, error)
 
-func (f GetGRPCServerOptionsFunc) GetGRPCServerOptions() ([]grpc.ServerOption, error) {
+func (f GetGRPCServerOptionsFunc) GetGRPCServerOptions(ctx context.Context) ([]grpc.ServerOption, error) {
 	if f == nil {
 		return nil, nil
 	}
-	return f()
+	return f(ctx)
 }
diff --git a/extension/extensionmiddleware/server_test.go b/extension/extensionmiddleware/server_test.go
index eee61f5410e..14d6ed5c4a6 100644
--- a/extension/extensionmiddleware/server_test.go
+++ b/extension/extensionmiddleware/server_test.go
@@ -66,9 +66,16 @@ func TestGetHTTPHandlerFunc(t *testing.T) {
 }
 
 func TestGetGRPCServerOptionsFunc(t *testing.T) {
+	type testCtx struct{}
+	var (
+		key   = testCtx{}
+		value = "testval"
+	)
+	testctx := context.WithValue(context.Background(), key, value)
+
 	t.Run("nil_function", func(t *testing.T) {
 		var f GetGRPCServerOptionsFunc
-		opts, err := f.GetGRPCServerOptions()
+		opts, err := f.GetGRPCServerOptions(testctx)
 		require.NoError(t, err)
 		require.Nil(t, opts)
 	})
@@ -84,22 +91,24 @@ func TestGetGRPCServerOptionsFunc(t *testing.T) {
 		}
 		expectedOpts := []grpc.ServerOption{grpc.UnaryInterceptor(interceptor)}
 
-		f := GetGRPCServerOptionsFunc(func() ([]grpc.ServerOption, error) {
+		f := GetGRPCServerOptionsFunc(func(ctx context.Context) ([]grpc.ServerOption, error) {
+			require.Equal(t, ctx.Value(key), value)
 			return expectedOpts, nil
 		})
 
-		opts, err := f.GetGRPCServerOptions()
+		opts, err := f.GetGRPCServerOptions(testctx)
 		require.NoError(t, err)
 		require.Equal(t, expectedOpts, opts)
 	})
 
 	t.Run("returns_error", func(t *testing.T) {
 		expectedErr := errors.New("test error")
-		f := GetGRPCServerOptionsFunc(func() ([]grpc.ServerOption, error) {
+		f := GetGRPCServerOptionsFunc(func(ctx context.Context) ([]grpc.ServerOption, error) {
+			require.Equal(t, ctx.Value(key), value)
 			return nil, expectedErr
 		})
 
-		opts, err := f.GetGRPCServerOptions()
+		opts, err := f.GetGRPCServerOptions(testctx)
 		require.Equal(t, expectedErr, err)
 		require.Nil(t, opts)
 	})
diff --git a/extension/memorylimiterextension/memorylimiter.go b/extension/memorylimiterextension/memorylimiter.go
index 319c2741d82..fd86cf96234 100644
--- a/extension/memorylimiterextension/memorylimiter.go
+++ b/extension/memorylimiterextension/memorylimiter.go
@@ -59,7 +59,7 @@ func (ml *memoryLimiterExtension) GetHTTPHandler(base http.Handler) (http.Handle
 	}), nil
 }
 
-func (ml *memoryLimiterExtension) GetGRPCServerOptions() ([]grpc.ServerOption, error) {
+func (ml *memoryLimiterExtension) GetGRPCServerOptions(_ context.Context) ([]grpc.ServerOption, error) {
 	return []grpc.ServerOption{
 		grpc.ChainUnaryInterceptor(
 			func(ctx context.Context, req any, _ *grpc.UnaryServerInfo, handler grpc.UnaryHandler) (resp any, err error) {