diff --git a/lib/pleroma/helpers/auth_helper.ex b/lib/pleroma/helpers/auth_helper.ex
index 13e4c8158..d56f6f461 100644
--- a/lib/pleroma/helpers/auth_helper.ex
+++ b/lib/pleroma/helpers/auth_helper.ex
@@ -4,12 +4,9 @@
 
 defmodule Pleroma.Helpers.AuthHelper do
   alias Pleroma.Web.Plugs.OAuthScopesPlug
-  alias Plug.Conn
 
   import Plug.Conn
 
-  @oauth_token_session_key :oauth_token
-
   @doc """
   Skips OAuth permissions (scopes) checks, assigns nil `:token`.
   Intended to be used with explicit authentication and only when OAuth token cannot be determined.
@@ -28,19 +25,4 @@ def drop_auth_info(conn) do
     |> assign(:token, nil)
     |> put_private(:authentication_ignored, true)
   end
-
-  @doc "Gets OAuth token string from session"
-  def get_session_token(%Conn{} = conn) do
-    get_session(conn, @oauth_token_session_key)
-  end
-
-  @doc "Updates OAuth token string in session"
-  def put_session_token(%Conn{} = conn, token) when is_binary(token) do
-    put_session(conn, @oauth_token_session_key, token)
-  end
-
-  @doc "Deletes OAuth token string from session"
-  def delete_session_token(%Conn{} = conn) do
-    delete_session(conn, @oauth_token_session_key)
-  end
 end
diff --git a/lib/pleroma/web/mastodon_api/controllers/auth_controller.ex b/lib/pleroma/web/mastodon_api/controllers/auth_controller.ex
index 4920d65da..f415e5931 100644
--- a/lib/pleroma/web/mastodon_api/controllers/auth_controller.ex
+++ b/lib/pleroma/web/mastodon_api/controllers/auth_controller.ex
@@ -7,7 +7,6 @@ defmodule Pleroma.Web.MastodonAPI.AuthController do
 
   import Pleroma.Web.ControllerHelper, only: [json_response: 3]
 
-  alias Pleroma.Helpers.AuthHelper
   alias Pleroma.Helpers.UriHelper
   alias Pleroma.User
   alias Pleroma.Web.OAuth.App
@@ -34,7 +33,6 @@ def login(conn, %{"code" => auth_token} = params) do
         |> UriHelper.modify_uri_params(%{"access_token" => oauth_token.token})
 
       conn
-      |> AuthHelper.put_session_token(oauth_token.token)
       |> redirect(to: redirect_to)
     else
       _ -> redirect_to_oauth_form(conn, params)
@@ -42,9 +40,9 @@ def login(conn, %{"code" => auth_token} = params) do
   end
 
   def login(conn, params) do
-    with %{assigns: %{user: %User{}, token: %Token{app_id: app_id}}} <- conn,
+    with %{assigns: %{user: %User{}, token: %Token{app_id: app_id, token: token}}} <- conn,
          {:ok, %{id: ^app_id}} <- local_mastofe_app() do
-      redirect(conn, to: local_mastodon_post_login_path(conn))
+      redirect(conn, to: local_mastodon_post_login_path(conn) <> "?access_token=#{token}")
     else
       _ -> redirect_to_oauth_form(conn, params)
     end
@@ -68,9 +66,8 @@ defp redirect_to_oauth_form(conn, _params) do
   def logout(conn, _) do
     conn =
       with %{assigns: %{token: %Token{} = oauth_token}} <- conn,
-           session_token = AuthHelper.get_session_token(conn),
-           {:ok, %Token{token: ^session_token}} <- RevokeToken.revoke(oauth_token) do
-        AuthHelper.delete_session_token(conn)
+           {:ok, %Token{token: _session_token}} <- RevokeToken.revoke(oauth_token) do
+        conn
       else
         _ -> conn
       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..43536f95d 100644
--- a/lib/pleroma/web/o_auth/o_auth_controller.ex
+++ b/lib/pleroma/web/o_auth/o_auth_controller.ex
@@ -5,7 +5,6 @@
 defmodule Pleroma.Web.OAuth.OAuthController do
   use Pleroma.Web, :controller
 
-  alias Pleroma.Helpers.AuthHelper
   alias Pleroma.Helpers.UriHelper
   alias Pleroma.Maps
   alias Pleroma.MFA
@@ -77,33 +76,46 @@ defp do_authorize(%Plug.Conn{} = conn, params) do
     available_scopes = (app && app.scopes) || []
     scopes = Scopes.fetch_scopes(params, available_scopes)
 
-    user =
-      with %{assigns: %{user: %User{} = user}} <- conn do
-        user
-      else
-        _ -> nil
-      end
+    # if we already have a token for this specific setup, we can use that
+    with false <- Params.truthy_param?(params["force_login"]),
+         %App{} <- app,
+         {:ok, _} <- Scopes.validate(scopes, app.scopes),
+         {:ok, %Token{} = token} <- Token.get_by_app(app) do
+      token = Repo.preload(token, :app)
 
-    scopes =
-      if scopes == [] do
-        available_scopes
-      else
-        scopes
-      end
+      conn
+      |> assign(:token, token)
+      |> handle_existing_authorization(params)
+    else
+      _ ->
+        user =
+          with %{assigns: %{user: %User{} = user}} <- conn do
+            user
+          else
+            _ -> nil
+          end
 
-    # Note: `params` might differ from `conn.params`; use `@params` not `@conn.params` in template
-    render(conn, Authenticator.auth_template(), %{
-      user: user,
-      app: app && Map.delete(app, :client_secret),
-      response_type: params["response_type"],
-      client_id: params["client_id"],
-      available_scopes: available_scopes,
-      scopes: scopes,
-      redirect_uri: params["redirect_uri"],
-      state: params["state"],
-      params: params,
-      view_module: OAuthView
-    })
+        scopes =
+          if scopes == [] do
+            available_scopes
+          else
+            scopes
+          end
+
+        # Note: `params` might differ from `conn.params`; use `@params` not `@conn.params` in template
+        render(conn, Authenticator.auth_template(), %{
+          user: user,
+          app: app && Map.delete(app, :client_secret),
+          response_type: params["response_type"],
+          client_id: params["client_id"],
+          available_scopes: available_scopes,
+          scopes: scopes,
+          redirect_uri: params["redirect_uri"],
+          state: params["state"],
+          params: params,
+          view_module: OAuthView
+        })
+    end
   end
 
   defp handle_existing_authorization(
@@ -318,9 +330,8 @@ def token_exchange(%Plug.Conn{} = conn, %{"grant_type" => "client_credentials"}
   # Bad request
   def token_exchange(%Plug.Conn{} = conn, params), do: bad_request(conn, params)
 
-  def after_token_exchange(%Plug.Conn{} = conn, %{token: token} = view_params) do
+  def after_token_exchange(%Plug.Conn{} = conn, %{token: _token} = view_params) do
     conn
-    |> AuthHelper.put_session_token(token.token)
     |> json(OAuthView.render("token.json", view_params))
   end
 
@@ -379,15 +390,7 @@ defp handle_token_exchange_error(%Plug.Conn{} = conn, _error) do
 
   def token_revoke(%Plug.Conn{} = conn, %{"token" => token}) do
     with {:ok, %Token{} = oauth_token} <- Token.get_by_token(token),
-         {:ok, oauth_token} <- RevokeToken.revoke(oauth_token) do
-      conn =
-        with session_token = AuthHelper.get_session_token(conn),
-             %Token{token: ^session_token} <- oauth_token do
-          AuthHelper.delete_session_token(conn)
-        else
-          _ -> conn
-        end
-
+         {:ok, _oauth_token} <- RevokeToken.revoke(oauth_token) do
       json(conn, %{})
     else
       _error ->
diff --git a/lib/pleroma/web/o_auth/token.ex b/lib/pleroma/web/o_auth/token.ex
index 9d69e9db4..08c8cd298 100644
--- a/lib/pleroma/web/o_auth/token.ex
+++ b/lib/pleroma/web/o_auth/token.ex
@@ -39,6 +39,12 @@ def get_by_token(token) do
     |> Repo.find_resource()
   end
 
+  def get_by_app(%App{} = app) do
+    app.id
+    |> Query.get_unexpired_by_app()
+    |> Repo.find_resource()
+  end
+
   @doc "Gets token for app by access token"
   @spec get_by_token(App.t(), String.t()) :: {:ok, t()} | {:error, :not_found}
   def get_by_token(%App{id: app_id} = _app, token) do
diff --git a/lib/pleroma/web/o_auth/token/query.ex b/lib/pleroma/web/o_auth/token/query.ex
index d16a759d8..8edfcf5d7 100644
--- a/lib/pleroma/web/o_auth/token/query.ex
+++ b/lib/pleroma/web/o_auth/token/query.ex
@@ -23,9 +23,15 @@ def get_by_token(query \\ Token, token) do
     from(q in query, where: q.token == ^token)
   end
 
+  @spec get_unexpired_by_app(query, String.t()) :: query
+  def get_unexpired_by_app(query \\ Token, app_id) do
+    time = NaiveDateTime.utc_now()
+    from(q in query, where: q.app_id == ^app_id and q.valid_until > ^time, limit: 1)
+  end
+
   @spec get_by_app(query, String.t()) :: query
   def get_by_app(query \\ Token, app_id) do
-    from(q in query, where: q.app_id == ^app_id)
+    from(q in query, where: q.app_id == ^app_id, limit: 1)
   end
 
   @spec get_by_id(query, String.t()) :: query
diff --git a/lib/pleroma/web/plugs/o_auth_plug.ex b/lib/pleroma/web/plugs/o_auth_plug.ex
index 5e06ac3f6..29b3316b3 100644
--- a/lib/pleroma/web/plugs/o_auth_plug.ex
+++ b/lib/pleroma/web/plugs/o_auth_plug.ex
@@ -8,7 +8,6 @@ defmodule Pleroma.Web.Plugs.OAuthPlug do
   import Plug.Conn
   import Ecto.Query
 
-  alias Pleroma.Helpers.AuthHelper
   alias Pleroma.Repo
   alias Pleroma.User
   alias Pleroma.Web.OAuth.App
@@ -18,8 +17,6 @@ defmodule Pleroma.Web.Plugs.OAuthPlug do
 
   def init(options), do: options
 
-  def call(%{assigns: %{user: %User{}}} = conn, _), do: conn
-
   def call(conn, _) do
     with {:ok, token_str} <- fetch_token_str(conn) do
       with {:ok, user, user_token} <- fetch_user_and_token(token_str),
@@ -82,7 +79,7 @@ defp fetch_token_str(%Plug.Conn{} = conn) do
     with {:ok, token} <- fetch_token_str(headers) do
       {:ok, token}
     else
-      _ -> fetch_token_from_session(conn)
+      _ -> :no_token_found
     end
   end
 
@@ -96,12 +93,4 @@ defp fetch_token_str([token | tail]) do
   end
 
   defp fetch_token_str([]), do: :no_token_found
-
-  @spec fetch_token_from_session(Plug.Conn.t()) :: :no_token_found | {:ok, String.t()}
-  defp fetch_token_from_session(conn) do
-    case AuthHelper.get_session_token(conn) do
-      nil -> :no_token_found
-      token -> {:ok, token}
-    end
-  end
 end
diff --git a/lib/pleroma/web/plugs/set_user_session_id_plug.ex b/lib/pleroma/web/plugs/set_user_session_id_plug.ex
deleted file mode 100644
index a1cfa0915..000000000
--- a/lib/pleroma/web/plugs/set_user_session_id_plug.ex
+++ /dev/null
@@ -1,18 +0,0 @@
-# Pleroma: A lightweight social networking server
-# Copyright © 2017-2021 Pleroma Authors <https://pleroma.social/>
-# SPDX-License-Identifier: AGPL-3.0-only
-
-defmodule Pleroma.Web.Plugs.SetUserSessionIdPlug do
-  alias Pleroma.Helpers.AuthHelper
-  alias Pleroma.Web.OAuth.Token
-
-  def init(opts) do
-    opts
-  end
-
-  def call(%{assigns: %{token: %Token{} = oauth_token}} = conn, _) do
-    AuthHelper.put_session_token(conn, oauth_token.token)
-  end
-
-  def call(conn, _), do: conn
-end
diff --git a/lib/pleroma/web/router.ex b/lib/pleroma/web/router.ex
index 647d99278..f2d6b0aff 100644
--- a/lib/pleroma/web/router.ex
+++ b/lib/pleroma/web/router.ex
@@ -57,7 +57,6 @@ defmodule Pleroma.Web.Router do
 
   pipeline :after_auth do
     plug(Pleroma.Web.Plugs.UserEnabledPlug)
-    plug(Pleroma.Web.Plugs.SetUserSessionIdPlug)
     plug(Pleroma.Web.Plugs.EnsureUserTokenAssignsPlug)
     plug(Pleroma.Web.Plugs.UserTrackingPlug)
   end
@@ -793,10 +792,8 @@ defmodule Pleroma.Web.Router do
 
     get("/web/login", MastodonAPI.AuthController, :login)
     delete("/auth/sign_out", MastodonAPI.AuthController, :logout)
-
-    post("/auth/password", MastodonAPI.AuthController, :password_reset)
-
     get("/web/*path", MastoFEController, :index)
+    post("/auth/password", MastodonAPI.AuthController, :password_reset)
 
     get("/embed/:id", EmbedController, :show)
   end
diff --git a/mix.exs b/mix.exs
index e7f491997..170276b0a 100644
--- a/mix.exs
+++ b/mix.exs
@@ -131,7 +131,7 @@ defp deps do
       {:trailing_format_plug, "~> 0.0.7"},
       {:fast_sanitize, "~> 0.2.3"},
       {:html_entities, "~> 0.5", override: true},
-      {:phoenix_html, "~> 3.1", override: true},
+      {:phoenix_html, "~> 3.0", override: true},
       {:calendar, "~> 1.0"},
       {:cachex, "~> 3.4"},
       {:poison, "~> 3.0", override: true},
@@ -152,7 +152,7 @@ defp deps do
        ref: "f75cd55325e33cbea198fb41fe41871392f8fb76"},
       {:cors_plug, "~> 2.0"},
       {:web_push_encryption, "~> 0.3.1"},
-      {:swoosh, "~> 1.0"},
+      {:swoosh, "~> 1.3"},
       {:phoenix_swoosh, "~> 0.3"},
       {:gen_smtp, "~> 0.13"},
       {:ex_syslogger, "~> 1.4"},
diff --git a/test/pleroma/web/o_auth/o_auth_controller_test.exs b/test/pleroma/web/o_auth/o_auth_controller_test.exs
index 0fdd5b8e9..4e197a485 100644
--- a/test/pleroma/web/o_auth/o_auth_controller_test.exs
+++ b/test/pleroma/web/o_auth/o_auth_controller_test.exs
@@ -7,7 +7,6 @@ defmodule Pleroma.Web.OAuth.OAuthControllerTest do
 
   import Pleroma.Factory
 
-  alias Pleroma.Helpers.AuthHelper
   alias Pleroma.MFA
   alias Pleroma.MFA.TOTP
   alias Pleroma.Repo
@@ -456,7 +455,7 @@ test "renders authentication page if user is already authenticated but `force_lo
 
       conn =
         conn
-        |> AuthHelper.put_session_token(token.token)
+        |> put_req_header("authorization", "Bearer #{token.token}")
         |> get(
           "/oauth/authorize",
           %{
@@ -480,7 +479,7 @@ test "renders authentication page if user is already authenticated but user requ
 
       conn =
         conn
-        |> AuthHelper.put_session_token(token.token)
+        |> put_req_header("authorization", "Bearer #{token.token}")
         |> get(
           "/oauth/authorize",
           %{
@@ -503,7 +502,7 @@ test "with existing authentication and non-OOB `redirect_uri`, redirects to app
 
       conn =
         conn
-        |> AuthHelper.put_session_token(token.token)
+        |> put_req_header("authorization", "Bearer #{token.token}")
         |> get(
           "/oauth/authorize",
           %{
@@ -529,7 +528,7 @@ test "with existing authentication and unlisted non-OOB `redirect_uri`, redirect
 
       conn =
         conn
-        |> AuthHelper.put_session_token(token.token)
+        |> put_req_header("authorization", "Bearer #{token.token}")
         |> get(
           "/oauth/authorize",
           %{
@@ -553,7 +552,7 @@ test "with existing authentication and OOB `redirect_uri`, redirects to app with
 
       conn =
         conn
-        |> AuthHelper.put_session_token(token.token)
+        |> put_req_header("authorization", "Bearer #{token.token}")
         |> get(
           "/oauth/authorize",
           %{
@@ -611,41 +610,6 @@ test "redirects with oauth authorization, " <>
       end
     end
 
-    test "authorize from cookie" do
-      user = insert(:user)
-      app = insert(:oauth_app)
-      oauth_token = insert(:oauth_token, user: user, app: app)
-      redirect_uri = OAuthController.default_redirect_uri(app)
-
-      conn =
-        build_conn()
-        |> Plug.Session.call(Plug.Session.init(@session_opts))
-        |> fetch_session()
-        |> AuthHelper.put_session_token(oauth_token.token)
-        |> post(
-          "/oauth/authorize",
-          %{
-            "authorization" => %{
-              "name" => user.nickname,
-              "client_id" => app.client_id,
-              "redirect_uri" => redirect_uri,
-              "scope" => app.scopes,
-              "state" => "statepassed"
-            }
-          }
-        )
-
-      target = redirected_to(conn)
-      assert target =~ redirect_uri
-
-      query = URI.parse(target).query |> URI.query_decoder() |> Map.new()
-
-      assert %{"state" => "statepassed", "code" => code} = query
-      auth = Repo.get_by(Authorization, token: code)
-      assert auth
-      assert auth.scopes == app.scopes
-    end
-
     test "redirect to on two-factor auth page" do
       otp_secret = TOTP.generate_secret()
 
@@ -1218,6 +1182,7 @@ test "issues a new token if token expired" do
 
       response =
         build_conn()
+        |> put_req_header("authorization", "Bearer #{access_token.token}")
         |> post("/oauth/token", %{
           "grant_type" => "refresh_token",
           "refresh_token" => access_token.refresh_token,
@@ -1267,12 +1232,11 @@ test "when authenticated with request token, revokes it and clears it from sessi
         build_conn()
         |> Plug.Session.call(Plug.Session.init(@session_opts))
         |> fetch_session()
-        |> AuthHelper.put_session_token(oauth_token.token)
+        |> put_req_header("authorization", "Bearer #{oauth_token.token}")
         |> post("/oauth/revoke", %{"token" => oauth_token.token})
 
       assert json_response(conn, 200)
 
-      refute AuthHelper.get_session_token(conn)
       assert Token.get_by_token(oauth_token.token) == {:error, :not_found}
     end
 
@@ -1286,12 +1250,11 @@ test "if request is authenticated with a different token, " <>
         build_conn()
         |> Plug.Session.call(Plug.Session.init(@session_opts))
         |> fetch_session()
-        |> AuthHelper.put_session_token(oauth_token.token)
+        |> put_req_header("authorization", "Bearer #{oauth_token.token}")
         |> post("/oauth/revoke", %{"token" => other_app_oauth_token.token})
 
       assert json_response(conn, 200)
 
-      assert AuthHelper.get_session_token(conn) == oauth_token.token
       assert Token.get_by_token(other_app_oauth_token.token) == {:error, :not_found}
     end
 
diff --git a/test/pleroma/web/plugs/o_auth_plug_test.exs b/test/pleroma/web/plugs/o_auth_plug_test.exs
index 9e4be5559..caabfc1cb 100644
--- a/test/pleroma/web/plugs/o_auth_plug_test.exs
+++ b/test/pleroma/web/plugs/o_auth_plug_test.exs
@@ -5,11 +5,8 @@
 defmodule Pleroma.Web.Plugs.OAuthPlugTest do
   use Pleroma.Web.ConnCase, async: true
 
-  alias Pleroma.Helpers.AuthHelper
   alias Pleroma.Web.OAuth.Token
-  alias Pleroma.Web.OAuth.Token.Strategy.Revoke
   alias Pleroma.Web.Plugs.OAuthPlug
-  alias Plug.Session
 
   import Pleroma.Factory
 
@@ -72,57 +69,4 @@ test "with invalid token, it does not assign the user", %{conn: conn} do
 
     refute conn.assigns[:user]
   end
-
-  describe "with :oauth_token in session, " do
-    setup %{token: oauth_token, conn: conn} do
-      session_opts = [
-        store: :cookie,
-        key: "_test",
-        signing_salt: "cooldude"
-      ]
-
-      conn =
-        conn
-        |> Session.call(Session.init(session_opts))
-        |> fetch_session()
-        |> AuthHelper.put_session_token(oauth_token.token)
-
-      %{conn: conn}
-    end
-
-    test "if session-stored token matches a valid OAuth token, assigns :user and :token", %{
-      conn: conn,
-      user: user,
-      token: oauth_token
-    } do
-      conn = OAuthPlug.call(conn, %{})
-
-      assert conn.assigns.user && conn.assigns.user.id == user.id
-      assert conn.assigns.token && conn.assigns.token.id == oauth_token.id
-    end
-
-    test "if session-stored token matches an expired OAuth token, does nothing", %{
-      conn: conn,
-      token: oauth_token
-    } do
-      expired_valid_until = NaiveDateTime.add(NaiveDateTime.utc_now(), -3600 * 24, :second)
-
-      oauth_token
-      |> Ecto.Changeset.change(valid_until: expired_valid_until)
-      |> Pleroma.Repo.update()
-
-      ret_conn = OAuthPlug.call(conn, %{})
-      assert ret_conn == conn
-    end
-
-    test "if session-stored token matches a revoked OAuth token, does nothing", %{
-      conn: conn,
-      token: oauth_token
-    } do
-      Revoke.revoke(oauth_token)
-
-      ret_conn = OAuthPlug.call(conn, %{})
-      assert ret_conn == conn
-    end
-  end
 end
diff --git a/test/pleroma/web/plugs/set_user_session_id_plug_test.exs b/test/pleroma/web/plugs/set_user_session_id_plug_test.exs
deleted file mode 100644
index 9814c80d8..000000000
--- a/test/pleroma/web/plugs/set_user_session_id_plug_test.exs
+++ /dev/null
@@ -1,43 +0,0 @@
-# Pleroma: A lightweight social networking server
-# Copyright © 2017-2021 Pleroma Authors <https://pleroma.social/>
-# SPDX-License-Identifier: AGPL-3.0-only
-
-defmodule Pleroma.Web.Plugs.SetUserSessionIdPlugTest do
-  use Pleroma.Web.ConnCase, async: true
-
-  alias Pleroma.Helpers.AuthHelper
-  alias Pleroma.Web.Plugs.SetUserSessionIdPlug
-
-  setup %{conn: conn} do
-    session_opts = [
-      store: :cookie,
-      key: "_test",
-      signing_salt: "cooldude"
-    ]
-
-    conn =
-      conn
-      |> Plug.Session.call(Plug.Session.init(session_opts))
-      |> fetch_session()
-
-    %{conn: conn}
-  end
-
-  test "doesn't do anything if the user isn't set", %{conn: conn} do
-    ret_conn = SetUserSessionIdPlug.call(conn, %{})
-
-    assert ret_conn == conn
-  end
-
-  test "sets session token basing on :token assign", %{conn: conn} do
-    %{user: user, token: oauth_token} = oauth_access(["read"])
-
-    ret_conn =
-      conn
-      |> assign(:user, user)
-      |> assign(:token, oauth_token)
-      |> SetUserSessionIdPlug.call(%{})
-
-    assert AuthHelper.get_session_token(ret_conn) == oauth_token.token
-  end
-end