diff --git a/lib/pleroma/helpers/auth_helper.ex b/lib/pleroma/helpers/auth_helper.ex
index 13e4c8158..37765da4d 100644
--- a/lib/pleroma/helpers/auth_helper.ex
+++ b/lib/pleroma/helpers/auth_helper.ex
@@ -9,6 +9,7 @@ defmodule Pleroma.Helpers.AuthHelper do
   import Plug.Conn
 
   @oauth_token_session_key :oauth_token
+  @oauth_user_session_key :oauth_user
 
   @doc """
   Skips OAuth permissions (scopes) checks, assigns nil `:token`.
@@ -43,4 +44,16 @@ def put_session_token(%Conn{} = conn, token) when is_binary(token) do
   def delete_session_token(%Conn{} = conn) do
     delete_session(conn, @oauth_token_session_key)
   end
+
+  def put_session_user(%Conn{} = conn, user) do
+    put_session(conn, @oauth_user_session_key, user)
+  end
+
+  def delete_session_user(%Conn{} = conn) do
+    delete_session(conn, @oauth_user_session_key)
+  end
+
+  def get_session_user(%Conn{} = conn) do
+    get_session(conn, @oauth_user_session_key)
+  end
 end
diff --git a/lib/pleroma/web/o_auth/o_auth_controller.ex b/lib/pleroma/web/o_auth/o_auth_controller.ex
index 358120fe6..45e99d35b 100644
--- a/lib/pleroma/web/o_auth/o_auth_controller.ex
+++ b/lib/pleroma/web/o_auth/o_auth_controller.ex
@@ -70,7 +70,21 @@ def authorize(
     end
   end
 
-  def authorize(%Plug.Conn{} = conn, params), do: do_authorize(conn, params)
+  def authorize(%Plug.Conn{} = conn, params) do
+    # if we have a user in the session, attempt to authenticate as them
+    # otherwise show the login form
+    with user_id <- AuthHelper.get_session_user(conn),
+         false <- is_nil(user_id),
+         %User{} = user <- User.get_cached_by_id(user_id),
+         %App{} = app <- Repo.get_by(App, client_id: params["client_id"]),
+         {:ok, %Token{} = token} <- Token.get_preeexisting_by_app_and_user(app, user) do
+      conn
+      |> assign(:token, token)
+      |> handle_existing_authorization(params)
+    else
+      _ -> do_authorize(conn, params)
+    end
+  end
 
   defp do_authorize(%Plug.Conn{} = conn, params) do
     app = Repo.get_by(App, client_id: params["client_id"])
@@ -148,7 +162,9 @@ def create_authorization(%Plug.Conn{assigns: %{user: %User{} = user}} = conn, pa
   def create_authorization(%Plug.Conn{} = conn, %{"authorization" => _} = params, opts) do
     with {:ok, auth, user} <- do_create_authorization(conn, params, opts[:user]),
          {:mfa_required, _, _, false} <- {:mfa_required, user, auth, MFA.require?(user)} do
-      after_create_authorization(conn, auth, params)
+      conn
+      |> AuthHelper.put_session_user(user.id)
+      |> after_create_authorization(auth, params)
     else
       error ->
         handle_create_authorization_error(conn, error, params)
@@ -321,6 +337,7 @@ def token_exchange(%Plug.Conn{} = conn, params), do: bad_request(conn, params)
   def after_token_exchange(%Plug.Conn{} = conn, %{token: token} = view_params) do
     conn
     |> AuthHelper.put_session_token(token.token)
+    |> AuthHelper.put_session_user(token.user_id)
     |> json(OAuthView.render("token.json", view_params))
   end
 
diff --git a/lib/pleroma/web/o_auth/token.ex b/lib/pleroma/web/o_auth/token.ex
index 9d69e9db4..686e6715b 100644
--- a/lib/pleroma/web/o_auth/token.ex
+++ b/lib/pleroma/web/o_auth/token.ex
@@ -70,6 +70,15 @@ def exchange_token(app, auth) do
     end
   end
 
+  def get_preeexisting_by_app_and_user(app, user) do
+    Query.get_by_app(app.id)
+    |> Query.get_by_user(user.id)
+    |> Query.get_unexpired()
+    |> Query.preload([:user])
+    |> Query.limit(1)
+    |> Repo.find_resource()
+  end
+
   defp put_token(changeset) do
     changeset
     |> change(%{token: Token.Utils.generate_token()})
diff --git a/lib/pleroma/web/o_auth/token/query.ex b/lib/pleroma/web/o_auth/token/query.ex
index d16a759d8..1415191b7 100644
--- a/lib/pleroma/web/o_auth/token/query.ex
+++ b/lib/pleroma/web/o_auth/token/query.ex
@@ -38,6 +38,15 @@ def get_by_user(query \\ Token, user_id) do
     from(q in query, where: q.user_id == ^user_id)
   end
 
+  def get_unexpired(query) do
+    now = NaiveDateTime.utc_now()
+    from(q in query, where: q.valid_until > ^now)
+  end
+
+  def limit(query, limit) do
+    from(q in query, limit: ^limit)
+  end
+
   @spec preload(query, any) :: query
   def preload(query \\ Token, assoc_preload \\ [])