diff --git a/changelog.d/gun_pool.fix b/changelog.d/gun_pool.fix
new file mode 100644
index 000000000..94ec9103d
--- /dev/null
+++ b/changelog.d/gun_pool.fix
@@ -0,0 +1 @@
+Fix logic error in Gun connection pooling which prevented retries even when the worker was launched with retry = true
diff --git a/lib/pleroma/gun/connection_pool/worker_supervisor.ex b/lib/pleroma/gun/connection_pool/worker_supervisor.ex
index b2be4ff87..24ad61117 100644
--- a/lib/pleroma/gun/connection_pool/worker_supervisor.ex
+++ b/lib/pleroma/gun/connection_pool/worker_supervisor.ex
@@ -21,7 +21,9 @@ def init(_opts) do
   def start_worker(opts, retry \\ false) do
     case DynamicSupervisor.start_child(__MODULE__, {Pleroma.Gun.ConnectionPool.Worker, opts}) do
       {:error, :max_children} ->
-        if Enum.any?([retry, free_pool()], &match?(&1, :error)) do
+        funs = [fn -> !retry end, fn -> match?(:error, free_pool()) end]
+
+        if Enum.any?(funs, fn fun -> fun.() end) do
           :telemetry.execute([:pleroma, :connection_pool, :provision_failure], %{opts: opts})
           {:error, :pool_full}
         else