diff --git a/config/config.exs b/config/config.exs
index 246712b9f..ea8869d48 100644
--- a/config/config.exs
+++ b/config/config.exs
@@ -740,19 +740,23 @@ config :pleroma, :connections_pool,
 config :pleroma, :pools,
   federation: [
     size: 50,
-    max_waiting: 10
+    max_waiting: 10,
+    timeout: 10_000
   ],
   media: [
     size: 50,
-    max_waiting: 10
+    max_waiting: 10,
+    timeout: 10_000
   ],
   upload: [
     size: 25,
-    max_waiting: 5
+    max_waiting: 5,
+    timeout: 15_000
   ],
   default: [
     size: 10,
-    max_waiting: 2
+    max_waiting: 2,
+    timeout: 5_000
   ]
 
 config :pleroma, :hackney_pools,
diff --git a/lib/pleroma/gun/connection_pool/worker.ex b/lib/pleroma/gun/connection_pool/worker.ex
index fec9d0efa..c36332817 100644
--- a/lib/pleroma/gun/connection_pool/worker.ex
+++ b/lib/pleroma/gun/connection_pool/worker.ex
@@ -83,17 +83,25 @@ defmodule Pleroma.Gun.ConnectionPool.Worker do
       end)
 
     {ref, state} = pop_in(state.client_monitors[client_pid])
-    Process.demonitor(ref)
-
-    timer =
-      if used_by == [] do
-        max_idle = Pleroma.Config.get([:connections_pool, :max_idle_time], 30_000)
-        Process.send_after(self(), :idle_close, max_idle)
+    # DOWN message can receive right after `remove_client` call and cause worker to terminate
+    state =
+      if is_nil(ref) do
+        state
       else
-        nil
+        Process.demonitor(ref)
+
+        timer =
+          if used_by == [] do
+            max_idle = Pleroma.Config.get([:connections_pool, :max_idle_time], 30_000)
+            Process.send_after(self(), :idle_close, max_idle)
+          else
+            nil
+          end
+
+        %{state | timer: timer}
       end
 
-    {:reply, :ok, %{state | timer: timer}, :hibernate}
+    {:reply, :ok, state, :hibernate}
   end
 
   @impl true
@@ -103,16 +111,21 @@ defmodule Pleroma.Gun.ConnectionPool.Worker do
     {:stop, :normal, state}
   end
 
+  @impl true
+  def handle_info({:gun_up, _pid, _protocol}, state) do
+    {:noreply, state, :hibernate}
+  end
+
   # Gracefully shutdown if the connection got closed without any streams left
   @impl true
   def handle_info({:gun_down, _pid, _protocol, _reason, []}, state) do
     {:stop, :normal, state}
   end
 
-  # Otherwise, shutdown with an error
+  # Otherwise, wait for retry
   @impl true
-  def handle_info({:gun_down, _pid, _protocol, _reason, _killed_streams} = down_message, state) do
-    {:stop, {:error, down_message}, state}
+  def handle_info({:gun_down, _pid, _protocol, _reason, _killed_streams}, state) do
+    {:noreply, state, :hibernate}
   end
 
   @impl true
diff --git a/lib/pleroma/http/adapter_helper.ex b/lib/pleroma/http/adapter_helper.ex
index 9ec3836b0..740e6e9ff 100644
--- a/lib/pleroma/http/adapter_helper.ex
+++ b/lib/pleroma/http/adapter_helper.ex
@@ -10,6 +10,7 @@ defmodule Pleroma.HTTP.AdapterHelper do
 
   @type proxy_type() :: :socks4 | :socks5
   @type host() :: charlist() | :inet.ip_address()
+  @type pool() :: :federation | :upload | :media | :default
 
   alias Pleroma.Config
   alias Pleroma.HTTP.AdapterHelper
@@ -44,14 +45,13 @@ defmodule Pleroma.HTTP.AdapterHelper do
   @spec options(URI.t(), keyword()) :: keyword()
   def options(%URI{} = uri, opts \\ []) do
     @defaults
-    |> put_timeout()
     |> Keyword.merge(opts)
+    |> put_timeout()
     |> adapter_helper().options(uri)
   end
 
-  # For Hackney, this is the time a connection can stay idle in the pool.
-  # For Gun, this is the timeout to receive a message from Gun.
-  defp put_timeout(opts) do
+  @spec pool_timeout(pool()) :: non_neg_integer()
+  def pool_timeout(pool) do
     {config_key, default} =
       if adapter() == Tesla.Adapter.Gun do
         {:pools, Config.get([:pools, :default, :timeout], 5_000)}
@@ -59,9 +59,13 @@ defmodule Pleroma.HTTP.AdapterHelper do
         {:hackney_pools, 10_000}
       end
 
-    timeout = Config.get([config_key, opts[:pool], :timeout], default)
+    Config.get([config_key, pool, :timeout], default)
+  end
 
-    Keyword.merge(opts, timeout: timeout)
+  # For Hackney, this is the time a connection can stay idle in the pool.
+  # For Gun, this is the timeout to receive a message from Gun.
+  defp put_timeout(opts) do
+    Keyword.put_new(opts, :timeout, pool_timeout(opts[:pool]))
   end
 
   def get_conn(uri, opts), do: adapter_helper().get_conn(uri, opts)
diff --git a/lib/pleroma/http/adapter_helper/gun.ex b/lib/pleroma/http/adapter_helper/gun.ex
index b4ff8306c..db0a298b3 100644
--- a/lib/pleroma/http/adapter_helper/gun.ex
+++ b/lib/pleroma/http/adapter_helper/gun.ex
@@ -5,6 +5,7 @@
 defmodule Pleroma.HTTP.AdapterHelper.Gun do
   @behaviour Pleroma.HTTP.AdapterHelper
 
+  alias Pleroma.Config
   alias Pleroma.Gun.ConnectionPool
   alias Pleroma.HTTP.AdapterHelper
 
@@ -14,7 +15,7 @@ defmodule Pleroma.HTTP.AdapterHelper.Gun do
     connect_timeout: 5_000,
     domain_lookup_timeout: 5_000,
     tls_handshake_timeout: 5_000,
-    retry: 0,
+    retry: 1,
     retry_timeout: 1000,
     await_up_timeout: 5_000
   ]
@@ -22,10 +23,11 @@ defmodule Pleroma.HTTP.AdapterHelper.Gun do
   @spec options(keyword(), URI.t()) :: keyword()
   def options(incoming_opts \\ [], %URI{} = uri) do
     proxy =
-      Pleroma.Config.get([:http, :proxy_url])
+      [:http, :proxy_url]
+      |> Config.get()
       |> AdapterHelper.format_proxy()
 
-    config_opts = Pleroma.Config.get([:http, :adapter], [])
+    config_opts = Config.get([:http, :adapter], [])
 
     @defaults
     |> Keyword.merge(config_opts)
@@ -37,8 +39,7 @@ defmodule Pleroma.HTTP.AdapterHelper.Gun do
   defp add_scheme_opts(opts, %{scheme: "http"}), do: opts
 
   defp add_scheme_opts(opts, %{scheme: "https"}) do
-    opts
-    |> Keyword.put(:certificates_verification, true)
+    Keyword.put(opts, :certificates_verification, true)
   end
 
   @spec get_conn(URI.t(), keyword()) :: {:ok, keyword()} | {:error, atom()}
@@ -51,11 +52,11 @@ defmodule Pleroma.HTTP.AdapterHelper.Gun do
 
   @prefix Pleroma.Gun.ConnectionPool
   def limiter_setup do
-    wait = Pleroma.Config.get([:connections_pool, :connection_acquisition_wait])
-    retries = Pleroma.Config.get([:connections_pool, :connection_acquisition_retries])
+    wait = Config.get([:connections_pool, :connection_acquisition_wait])
+    retries = Config.get([:connections_pool, :connection_acquisition_retries])
 
     :pools
-    |> Pleroma.Config.get([])
+    |> Config.get([])
     |> Enum.each(fn {name, opts} ->
       max_running = Keyword.get(opts, :size, 50)
       max_waiting = Keyword.get(opts, :max_waiting, 10)
@@ -69,7 +70,6 @@ defmodule Pleroma.HTTP.AdapterHelper.Gun do
       case result do
         :ok -> :ok
         {:error, :existing} -> :ok
-        e -> raise e
       end
     end)
 
diff --git a/lib/pleroma/http/ex_aws.ex b/lib/pleroma/http/ex_aws.ex
index e53e64077..2fe8beafc 100644
--- a/lib/pleroma/http/ex_aws.ex
+++ b/lib/pleroma/http/ex_aws.ex
@@ -11,6 +11,8 @@ defmodule Pleroma.HTTP.ExAws do
 
   @impl true
   def request(method, url, body \\ "", headers \\ [], http_opts \\ []) do
+    http_opts = Keyword.put(http_opts, :adapter, pool: :upload)
+
     case HTTP.request(method, url, body, headers, http_opts) do
       {:ok, env} ->
         {:ok, %{status_code: env.status, headers: env.headers, body: env.body}}
diff --git a/lib/pleroma/http/tzdata.ex b/lib/pleroma/http/tzdata.ex
index 34bb253a7..7dd3352ff 100644
--- a/lib/pleroma/http/tzdata.ex
+++ b/lib/pleroma/http/tzdata.ex
@@ -11,6 +11,8 @@ defmodule Pleroma.HTTP.Tzdata do
 
   @impl true
   def get(url, headers, options) do
+    options = Keyword.put(options, :adapter, pool: :upload)
+
     with {:ok, %Tesla.Env{} = env} <- HTTP.get(url, headers, options) do
       {:ok, {env.status, env.headers, env.body}}
     end
@@ -18,6 +20,8 @@ defmodule Pleroma.HTTP.Tzdata do
 
   @impl true
   def head(url, headers, options) do
+    options = Keyword.put(options, :adapter, pool: :upload)
+
     with {:ok, %Tesla.Env{} = env} <- HTTP.head(url, headers, options) do
       {:ok, {env.status, env.headers}}
     end
diff --git a/lib/pleroma/uploaders/s3.ex b/lib/pleroma/uploaders/s3.ex
index a13ff23b6..ed9794ca2 100644
--- a/lib/pleroma/uploaders/s3.ex
+++ b/lib/pleroma/uploaders/s3.ex
@@ -46,12 +46,19 @@ defmodule Pleroma.Uploaders.S3 do
 
     op =
       if streaming do
-        upload.tempfile
-        |> ExAws.S3.Upload.stream_file()
-        |> ExAws.S3.upload(bucket, s3_name, [
-          {:acl, :public_read},
-          {:content_type, upload.content_type}
-        ])
+        op =
+          upload.tempfile
+          |> ExAws.S3.Upload.stream_file()
+          |> ExAws.S3.upload(bucket, s3_name, [
+            {:acl, :public_read},
+            {:content_type, upload.content_type}
+          ])
+
+        # set s3 upload timeout to respect :upload pool timeout
+        # timeout should be slightly larger, so s3 can retry upload on fail
+        timeout = Pleroma.HTTP.AdapterHelper.pool_timeout(:upload) + 1_000
+        opts = Keyword.put(op.opts, :timeout, timeout)
+        Map.put(op, :opts, opts)
       else
         {:ok, file_data} = File.read(upload.tempfile)