diff --git a/lib/pleroma/http/adapter/gun.ex b/lib/pleroma/http/adapter/gun.ex
index f1018dd8d..fc40b324a 100644
--- a/lib/pleroma/http/adapter/gun.ex
+++ b/lib/pleroma/http/adapter/gun.ex
@@ -115,11 +115,16 @@ defmodule Pleroma.HTTP.Adapter.Gun do
 
         opts
     catch
-      :exit, {:timeout, _} ->
+      :exit, {:timeout, {_, operation, [_, {method, _}, _]}} ->
+        messages_len =
+          :gun_connections
+          |> Process.whereis()
+          |> Process.info(:message_queue_len)
+
         Logger.warn(
-          "Gun connections pool checkin with timeout error #{uri.scheme}://#{
-            Connections.compose_uri(uri)
-          }"
+          "Gun connections pool checkin with timeout error for #{operation} #{method} #{
+            uri.scheme
+          }://#{Connections.compose_uri(uri)}. Messages length: #{messages_len}"
         )
 
         opts
diff --git a/test/http_test.exs b/test/http_test.exs
index d80b96496..83c27f6e1 100644
--- a/test/http_test.exs
+++ b/test/http_test.exs
@@ -61,8 +61,8 @@ defmodule Pleroma.HTTPTest do
 
   describe "connection pools" do
     @describetag :integration
-    clear_config([Pleroma.Gun.API]) do
-      Pleroma.Config.put([Pleroma.Gun.API], Pleroma.Gun)
+    clear_config(Pleroma.Gun.API) do
+      Pleroma.Config.put(Pleroma.Gun.API, Pleroma.Gun)
     end
 
     test "gun" do
diff --git a/test/pool/connections_test.exs b/test/pool/connections_test.exs
index 6f0e041ae..d0d711c55 100644
--- a/test/pool/connections_test.exs
+++ b/test/pool/connections_test.exs
@@ -15,6 +15,10 @@ defmodule Pleroma.Pool.ConnectionsTest do
     :ok
   end
 
+  clear_config([:connections_pool, :retry]) do
+    Pleroma.Config.put([:connections_pool, :retry], 5)
+  end
+
   setup do
     name = :test_connections
     adapter = Application.get_env(:tesla, :adapter)
@@ -429,8 +433,8 @@ defmodule Pleroma.Pool.ConnectionsTest do
   describe "integration test" do
     @describetag :integration
 
-    clear_config([API]) do
-      Pleroma.Config.put([API], Pleroma.Gun)
+    clear_config(API) do
+      Pleroma.Config.put(API, Pleroma.Gun)
     end
 
     test "opens connection and reuse it on next request", %{name: name} do
diff --git a/test/reverse_proxy/client/tesla_test.exs b/test/reverse_proxy/client/tesla_test.exs
index 75a70988c..231271b0d 100644
--- a/test/reverse_proxy/client/tesla_test.exs
+++ b/test/reverse_proxy/client/tesla_test.exs
@@ -8,8 +8,8 @@ defmodule Pleroma.ReverseProxy.Client.TeslaTest do
   alias Pleroma.ReverseProxy.Client
   @moduletag :integration
 
-  clear_config_all([Pleroma.Gun.API]) do
-    Pleroma.Config.put([Pleroma.Gun.API], Pleroma.Gun)
+  clear_config_all(Pleroma.Gun.API) do
+    Pleroma.Config.put(Pleroma.Gun.API, Pleroma.Gun)
   end
 
   setup do
diff --git a/test/reverse_proxy/reverse_proxy_test.exs b/test/reverse_proxy/reverse_proxy_test.exs
index 1ab3cc4bb..f61fc02c5 100644
--- a/test/reverse_proxy/reverse_proxy_test.exs
+++ b/test/reverse_proxy/reverse_proxy_test.exs
@@ -345,12 +345,12 @@ defmodule Pleroma.ReverseProxyTest do
   describe "tesla client using gun integration" do
     @describetag :integration
 
-    clear_config([Pleroma.ReverseProxy.Client]) do
-      Pleroma.Config.put([Pleroma.ReverseProxy.Client], Pleroma.ReverseProxy.Client.Tesla)
+    clear_config(Pleroma.ReverseProxy.Client) do
+      Pleroma.Config.put(Pleroma.ReverseProxy.Client, Pleroma.ReverseProxy.Client.Tesla)
     end
 
-    clear_config([Pleroma.Gun.API]) do
-      Pleroma.Config.put([Pleroma.Gun.API], Pleroma.Gun)
+    clear_config(Pleroma.Gun.API) do
+      Pleroma.Config.put(Pleroma.Gun.API, Pleroma.Gun)
     end
 
     setup do