diff --git a/sessions/TODO b/sessions/TODO
new file mode 100644
index 0000000..16f8b4f
--- /dev/null
+++ b/sessions/TODO
@@ -0,0 +1,4 @@
+- Update Session data to use defined types instead of string map
+- Create type assertions for Session data
+- Refactor functions to use newly defined types + assertions
+- Phase in new_context.go functions over context.go
\ No newline at end of file
diff --git a/sessions/new_context.go b/sessions/new_context.go
new file mode 100644
index 0000000..528db09
--- /dev/null
+++ b/sessions/new_context.go
@@ -0,0 +1,92 @@
+package sessions
+
+import (
+	"context"
+
+	"github.com/pkg/errors"
+
+	"github.com/theopenlane/utils/contextx"
+	"golang.org/x/oauth2"
+)
+
+// NewContextWithToken returns a copy of ctx that stores the Token
+func NewContextWithToken(ctx context.Context, token *oauth2.Token) context.Context {
+	return contextx.With(ctx, token)
+}
+
+// NewOhAuthTokenFromContext returns the Token from the ctx
+func NewOhAuthTokenFromContext(ctx context.Context) (*oauth2.Token, error) {
+	token, ok := contextx.From[*oauth2.Token](ctx)
+	if !ok {
+		return nil, errors.New("context missing Token")
+	}
+
+	return token, nil
+}
+
+// NewUserIDFromContext returns the user ID from the ctx
+// this function assumes the session data is stored in a string map
+func NewUserIDFromContext(ctx context.Context) (string, error) {
+	sessionDetails, ok := contextx.From[*Session[any]](ctx)
+	if !ok {
+		return "", ErrInvalidSession
+	}
+
+	sessionID := sessionDetails.GetKey()
+
+	sessionData, ok := sessionDetails.GetOk(sessionID)
+	if !ok {
+		return "", ErrInvalidSession
+	}
+
+	sd, ok := sessionData.(map[string]string)
+	if !ok {
+		return "", ErrInvalidSession
+	}
+
+	userID, ok := sd["userID"]
+	if !ok {
+		return "", ErrInvalidSession
+	}
+
+	return userID, nil
+}
+
+type UserID string
+
+// NewContextWithUserID returns a copy of ctx that stores the user ID
+func NewContextWithUserID(ctx context.Context, userID UserID) context.Context {
+	if userID == "" {
+		return ctx
+	}
+
+	return contextx.With(ctx, userID)
+}
+
+// NewSessionToken returns the session token from the context
+func NewSessionToken(ctx context.Context) (string, error) {
+	sd, err := newGetSessionDataFromContext(ctx)
+	if err != nil {
+		return "", err
+	}
+
+	sd.mu.Lock()
+	defer sd.mu.Unlock()
+
+	return sd.store.EncodeCookie(sd)
+}
+
+// NewAddSessionDataToContext adds session data to the context
+func (s *Session[P]) NewAddSessionDataToContext(ctx context.Context) context.Context {
+	return contextx.With(ctx, s)
+}
+
+// newGetSessionDataFromContext retrieves session data from the context
+func newGetSessionDataFromContext(ctx context.Context) (*Session[map[string]any], error) {
+	sessionData, ok := contextx.From[*Session[map[string]any]](ctx)
+	if !ok {
+		return nil, errors.New("context missing session data")
+	}
+
+	return sessionData, nil
+}
diff --git a/sessions/newcontext_test.go b/sessions/newcontext_test.go
new file mode 100644
index 0000000..c1c6c2a
--- /dev/null
+++ b/sessions/newcontext_test.go
@@ -0,0 +1,74 @@
+package sessions_test
+
+import (
+	"context"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/theopenlane/utils/contextx"
+	"golang.org/x/oauth2"
+
+	"github.com/theopenlane/iam/sessions"
+)
+
+func TestNewContextWithToken(t *testing.T) {
+	ctx := context.Background()
+	token := &oauth2.Token{AccessToken: "test_token"}
+
+	ctx = sessions.NewContextWithToken(ctx, token)
+	retrievedToken, ok := contextx.From[*oauth2.Token](ctx)
+
+	assert.True(t, ok)
+	assert.Equal(t, token, retrievedToken)
+}
+
+func TestNewOhAuthTokenFromContext(t *testing.T) {
+	ctx := context.Background()
+	token := &oauth2.Token{AccessToken: "test_token"}
+
+	ctx = sessions.NewContextWithToken(ctx, token)
+	retrievedToken, err := sessions.NewOhAuthTokenFromContext(ctx)
+
+	assert.NoError(t, err)
+	assert.Equal(t, token, retrievedToken)
+}
+
+func TestNewOhAuthTokenFromContext_MissingToken(t *testing.T) {
+	ctx := context.Background()
+
+	_, err := sessions.NewOhAuthTokenFromContext(ctx)
+
+	assert.Error(t, err)
+	assert.Equal(t, "context missing Token", err.Error())
+}
+
+func TestNewUserIDFromContext_MissingSession(t *testing.T) {
+	ctx := context.Background()
+
+	_, err := sessions.NewUserIDFromContext(ctx)
+
+	assert.Error(t, err)
+	assert.Equal(t, sessions.ErrInvalidSession, err)
+}
+
+func TestNewContextWithUserID(t *testing.T) {
+	ctx := context.Background()
+	userID := sessions.UserID("test_user")
+
+	ctx = sessions.NewContextWithUserID(ctx, userID)
+	retrievedUserID, ok := contextx.From[sessions.UserID](ctx)
+
+	assert.True(t, ok)
+	assert.Equal(t, userID, retrievedUserID)
+}
+
+func TestNewContextWithUserID_EmptyUserID(t *testing.T) {
+	ctx := context.Background()
+	userID := sessions.UserID("")
+
+	ctx = sessions.NewContextWithUserID(ctx, userID)
+	retrievedUserID, ok := contextx.From[sessions.UserID](ctx)
+
+	assert.False(t, ok)
+	assert.Equal(t, sessions.UserID(""), retrievedUserID)
+}