diff --git a/changelog.d/dialyzer5.skip b/changelog.d/dialyzer5.skip
new file mode 100644
index 000000000..e69de29bb
diff --git a/changelog.d/rich-media-hardening.fix b/changelog.d/rich-media-hardening.fix
new file mode 100644
index 000000000..ff3dc81f3
--- /dev/null
+++ b/changelog.d/rich-media-hardening.fix
@@ -0,0 +1 @@
+Harden Rich Media parsing against very slow or malicious URLs
diff --git a/config/config.exs b/config/config.exs
index 3058160ea..2f0d9d7d2 100644
--- a/config/config.exs
+++ b/config/config.exs
@@ -448,7 +448,7 @@
     Pleroma.Web.RichMedia.Parsers.TwitterCard,
     Pleroma.Web.RichMedia.Parsers.OEmbed
   ],
-  failure_backoff: 60_000,
+  timeout: 5_000,
   ttl_setters: [
     Pleroma.Web.RichMedia.Parser.TTL.AwsSignedUrl,
     Pleroma.Web.RichMedia.Parser.TTL.Opengraph
@@ -580,6 +580,8 @@
   ],
   email_blacklist: []
 
+# The Pruner :max_age must be longer than Worker :unique
+# value or it cannot enforce uniqueness.
 config :pleroma, Oban,
   repo: Pleroma.Repo,
   log: false,
@@ -593,7 +595,7 @@
     search_indexing: [limit: 10, paused: true],
     slow: 5
   ],
-  plugins: [Oban.Plugins.Pruner],
+  plugins: [{Oban.Plugins.Pruner, max_age: 900}],
   crontab: [
     {"0 0 * * 0", Pleroma.Workers.Cron.DigestEmailsWorker},
     {"0 0 * * *", Pleroma.Workers.Cron.NewUsersDigestWorker}
diff --git a/config/description.exs b/config/description.exs
index 179eea3f7..2809e9130 100644
--- a/config/description.exs
+++ b/config/description.exs
@@ -2101,11 +2101,11 @@
         ]
       },
       %{
-        key: :failure_backoff,
+        key: :timeout,
         type: :integer,
         description:
-          "Amount of milliseconds after request failure, during which the request will not be retried.",
-        suggestions: [60_000]
+          "Amount of milliseconds after which the HTTP request is forcibly terminated.",
+        suggestions: [5_000]
       }
     ]
   },
diff --git a/config/test.exs b/config/test.exs
index 2a007a22d..723bbc8e6 100644
--- a/config/test.exs
+++ b/config/test.exs
@@ -187,6 +187,8 @@
 config :pleroma, Pleroma.Web.RichMedia.Backfill,
   stream_out: Pleroma.Web.ActivityPub.ActivityPubMock
 
+config :pleroma, Pleroma.Web.Plugs.HTTPSecurityPlug, enable: false
+
 config :pleroma, Pleroma.User.Backup, tempdir: "test/tmp"
 
 if File.exists?("./config/test.secret.exs") do
diff --git a/docs/configuration/cheatsheet.md b/docs/configuration/cheatsheet.md
index 5689d3be5..0b4e53b6f 100644
--- a/docs/configuration/cheatsheet.md
+++ b/docs/configuration/cheatsheet.md
@@ -436,7 +436,7 @@ config :pleroma, Pleroma.Web.MediaProxy.Invalidation.Http,
 * `ignore_hosts`: list of hosts which will be ignored by the metadata parser. For example `["accounts.google.com", "xss.website"]`, defaults to `[]`.
 * `ignore_tld`: list TLDs (top-level domains) which will ignore for parse metadata. default is ["local", "localdomain", "lan"].
 * `parsers`: list of Rich Media parsers.
-* `failure_backoff`: Amount of milliseconds after request failure, during which the request will not be retried.
+* `timeout`: Amount of milliseconds after which the HTTP request is forcibly terminated.
 
 ## HTTP server
 
diff --git a/lib/pleroma/application.ex b/lib/pleroma/application.ex
index d98293e8e..cb15dc1e9 100644
--- a/lib/pleroma/application.ex
+++ b/lib/pleroma/application.ex
@@ -14,7 +14,6 @@ defmodule Pleroma.Application do
   @name Mix.Project.config()[:name]
   @version Mix.Project.config()[:version]
   @repository Mix.Project.config()[:source_url]
-  @compile_env Mix.env()
 
   def name, do: @name
   def version, do: @version
@@ -53,7 +52,7 @@ def start(_type, _args) do
     Pleroma.Config.Oban.warn()
     Config.DeprecationWarnings.warn()
 
-    if @compile_env != :test do
+    if Config.get([Pleroma.Web.Plugs.HTTPSecurityPlug, :enable], true) do
       Pleroma.Web.Plugs.HTTPSecurityPlug.warn_if_disabled()
     end
 
diff --git a/lib/pleroma/http.ex b/lib/pleroma/http.ex
index ec837e509..c11317850 100644
--- a/lib/pleroma/http.ex
+++ b/lib/pleroma/http.ex
@@ -68,7 +68,9 @@ def request(method, url, body, headers, options) when is_binary(url) do
 
     adapter = Application.get_env(:tesla, :adapter)
 
-    client = Tesla.client(adapter_middlewares(adapter), adapter)
+    extra_middleware = options[:tesla_middleware] || []
+
+    client = Tesla.client(adapter_middlewares(adapter, extra_middleware), adapter)
 
     maybe_limit(
       fn ->
@@ -102,20 +104,21 @@ defp maybe_limit(fun, _, _) do
     fun.()
   end
 
-  defp adapter_middlewares(Tesla.Adapter.Gun) do
-    [Tesla.Middleware.FollowRedirects, Pleroma.Tesla.Middleware.ConnectionPool]
+  defp adapter_middlewares(Tesla.Adapter.Gun, extra_middleware) do
+    [Tesla.Middleware.FollowRedirects, Pleroma.Tesla.Middleware.ConnectionPool] ++
+      extra_middleware
   end
 
-  defp adapter_middlewares({Tesla.Adapter.Finch, _}) do
-    [Tesla.Middleware.FollowRedirects]
+  defp adapter_middlewares({Tesla.Adapter.Finch, _}, extra_middleware) do
+    [Tesla.Middleware.FollowRedirects] ++ extra_middleware
   end
 
-  defp adapter_middlewares(_) do
+  defp adapter_middlewares(_, extra_middleware) do
     if Pleroma.Config.get(:env) == :test do
       # Emulate redirects in test env, which are handled by adapters in other environments
       [Tesla.Middleware.FollowRedirects]
     else
-      []
+      extra_middleware
     end
   end
 end
diff --git a/lib/pleroma/web/rich_media/backfill.ex b/lib/pleroma/web/rich_media/backfill.ex
index a66422e71..1cd90629f 100644
--- a/lib/pleroma/web/rich_media/backfill.ex
+++ b/lib/pleroma/web/rich_media/backfill.ex
@@ -36,13 +36,9 @@ def run(%{"url" => url} = args) do
         :ok
 
       {:error, type} = error
-      when type in [:invalid_metadata, :body_too_large, :content_type, :validate] ->
+      when type in [:invalid_metadata, :body_too_large, :content_type, :validate, :get, :head] ->
         negative_cache(url_hash)
         error
-
-      {:error, type} = error
-      when type in [:get, :head] ->
-        error
     end
   end
 
@@ -68,5 +64,5 @@ defp stream_update(%{"activity_id" => activity_id}) do
   defp warm_cache(key, val), do: @cachex.put(:rich_media_cache, key, val)
 
   defp negative_cache(key, ttl \\ :timer.minutes(15)),
-    do: @cachex.put(:rich_media_cache, key, nil, ttl: ttl)
+    do: @cachex.put(:rich_media_cache, key, :error, ttl: ttl)
 end
diff --git a/lib/pleroma/web/rich_media/helpers.ex b/lib/pleroma/web/rich_media/helpers.ex
index fba23c657..e2889b351 100644
--- a/lib/pleroma/web/rich_media/helpers.ex
+++ b/lib/pleroma/web/rich_media/helpers.ex
@@ -69,9 +69,12 @@ defp check_content_length(headers) do
   end
 
   defp http_options do
+    timeout = Config.get!([:rich_media, :timeout])
+
     [
       pool: :rich_media,
-      max_body: Config.get([:rich_media, :max_body], 5_000_000)
+      max_body: Config.get([:rich_media, :max_body], 5_000_000),
+      tesla_middleware: [{Tesla.Middleware.Timeout, timeout: timeout}]
     ]
   end
 end
diff --git a/lib/pleroma/workers/rich_media_worker.ex b/lib/pleroma/workers/rich_media_worker.ex
index 30f9d9e9e..2ebf42d4f 100644
--- a/lib/pleroma/workers/rich_media_worker.ex
+++ b/lib/pleroma/workers/rich_media_worker.ex
@@ -3,6 +3,7 @@
 # SPDX-License-Identifier: AGPL-3.0-only
 
 defmodule Pleroma.Workers.RichMediaWorker do
+  alias Pleroma.Config
   alias Pleroma.Web.RichMedia.Backfill
   alias Pleroma.Web.RichMedia.Card
 
@@ -19,18 +20,21 @@ def perform(%Job{args: %{"op" => "backfill", "url" => _url} = args}) do
         :ok
 
       {:error, type}
-      when type in [:invalid_metadata, :body_too_large, :content_type, :validate] ->
+      when type in [:invalid_metadata, :body_too_large, :content_type, :validate, :get, :head] ->
         {:cancel, type}
 
-      {:error, type}
-      when type in [:get, :head] ->
-        {:error, type}
-
       error ->
         {:error, error}
     end
   end
 
+  # There is timeout value enforced by Tesla.Middleware.Timeout
+  # which can be found in the RichMedia.Helpers module to allow us to detect
+  # a slow/infinite data stream and insert a negative cache entry for the URL
+  # We pad it by 2 seconds to be certain a slow connection is detected and we
+  # can inject a negative cache entry for the URL
   @impl Oban.Worker
-  def timeout(_job), do: :timer.seconds(5)
+  def timeout(_job) do
+    Config.get!([:rich_media, :timeout]) + :timer.seconds(2)
+  end
 end
diff --git a/test/pleroma/web/rich_media/backfill_test.exs b/test/pleroma/web/rich_media/backfill_test.exs
new file mode 100644
index 000000000..6d221fcf5
--- /dev/null
+++ b/test/pleroma/web/rich_media/backfill_test.exs
@@ -0,0 +1,26 @@
+# Pleroma: A lightweight social networking server
+# Copyright © 2017-2022 Pleroma Authors <https://pleroma.social/>
+# SPDX-License-Identifier: AGPL-3.0-only
+
+defmodule Pleroma.Web.RichMedia.BackfillTest do
+  use Pleroma.DataCase
+
+  alias Pleroma.Web.RichMedia.Backfill
+  alias Pleroma.Web.RichMedia.Card
+
+  import Mox
+
+  setup_all do: clear_config([:rich_media, :enabled], true)
+
+  test "sets a negative cache entry for an error" do
+    url = "https://bad.example.com/"
+    url_hash = Card.url_to_hash(url)
+
+    Tesla.Mock.mock(fn %{url: ^url} -> :error end)
+
+    Pleroma.CachexMock
+    |> expect(:put, fn :rich_media_cache, ^url_hash, :error, ttl: _ -> {:ok, true} end)
+
+    Backfill.run(%{"url" => url})
+  end
+end