diff --git a/lib/plausible_web/components/billing/plan_box.ex b/lib/plausible_web/components/billing/plan_box.ex
index 37e21b407645..69514703f3aa 100644
--- a/lib/plausible_web/components/billing/plan_box.ex
+++ b/lib/plausible_web/components/billing/plan_box.ex
@@ -39,7 +39,9 @@ defmodule PlausibleWeb.Components.Billing.PlanBox do
       <div>
         <.render_price_info available={@available} {assigns} />
         <%= if @available do %>
-          <.checkout id={"#{@kind}-checkout"} {assigns} />
+          <div class="relative">
+            <.checkout id={"#{@kind}-checkout"} {assigns} />
+          </div>
         <% else %>
           <.contact_button class="bg-indigo-600 hover:bg-indigo-500 text-white" />
         <% end %>
@@ -164,33 +166,36 @@ defmodule PlausibleWeb.Components.Billing.PlanBox do
       ])
 
     subscription_deleted = Subscription.Status.deleted?(subscription)
+    usage_within_limits = usage_within_plan_limits?(assigns)
 
-    {checkout_disabled, disabled_message} =
+    {checkout_disabled, disabled_message, limits} =
       cond do
         not assigns.eligible_for_upgrade? ->
-          {true, nil}
+          {true, nil, nil}
 
         change_plan_link_text == "Currently on this plan" && not subscription_deleted ->
-          {true, nil}
+          {true, nil, nil}
 
-        assigns.available && !usage_within_plan_limits?(assigns) ->
-          {true, "Your usage exceeds this plan"}
+        usage_within_limits != :ok ->
+          {true, "Your usage exceeds this plan", limits(usage_within_limits)}
 
         billing_details_expired ->
-          {true, "Please update your billing details first"}
+          {true, "Please update your billing details first", nil}
 
         true ->
-          {false, nil}
+          {false, nil, nil}
       end
 
     features_to_lose = assigns.usage.features -- assigns.plan_to_render.features
 
     assigns =
       assigns
+      |> assign(:display_tooltip_product_id, assigns[:display_tooltip_product_id])
       |> assign(:paddle_product_id, paddle_product_id)
       |> assign(:change_plan_link_text, change_plan_link_text)
       |> assign(:checkout_disabled, checkout_disabled)
       |> assign(:disabled_message, disabled_message)
+      |> assign(:disabled_message_limits, limits)
       |> assign(:confirm_message, losing_features_message(features_to_lose))
 
     ~H"""
@@ -201,13 +206,75 @@ defmodule PlausibleWeb.Components.Billing.PlanBox do
         Upgrade
       </PlausibleWeb.Components.Billing.paddle_button>
     <% end %>
-    <p :if={@disabled_message} class="h-0 text-center text-sm text-red-700 dark:text-red-500">
-      <%= @disabled_message %>
+    <p
+      :if={@disabled_message}
+      class="h-0 text-center text-sm text-red-700 dark:text-red-500 disabled-message"
+    >
+      <%= if @disabled_message_limits do %>
+        <.disabled_with_tooltip
+          show_tooltip?={@paddle_product_id == @display_tooltip_product_id}
+          paddle_product_id={@paddle_product_id}
+          disabled_message={@disabled_message}
+          limits={@disabled_message_limits}
+        />
+      <% else %>
+        <%= @disabled_message %>
+      <% end %>
     </p>
     """
   end
 
-  defp usage_within_plan_limits?(%{usage: usage, user: user, plan_to_render: plan}) do
+  attr :show_tooltip?, :boolean, default: false
+  attr :paddle_product_id, :string, required: true
+  attr :limits, :list, default: nil
+  attr :disabled_message, :string, required: true
+
+  def disabled_with_tooltip(assigns) do
+    opacity =
+      if assigns.show_tooltip? do
+        "opacity-90"
+      else
+        "opacity-0 group-hover:opacity-90"
+      end
+
+    assigns = assign(assigns, opacity: opacity)
+
+    ~H"""
+    <div class="text-sm text-red-700 dark:text-red-500 cursor-pointer mt-1 group tooltip-wrapper">
+      <span class={[
+        "bg-black pointer-events-none absolute bottom-10 margin-x-auto left-10 right-10 transition-opacity p-4 rounded text-white",
+        @opacity
+      ]}>
+        Your usage exceeds the following limit(s):<br /><br />
+        <%= for limit <- @limits do %>
+          <%= Phoenix.Naming.humanize(limit) %>
+        <% end %>
+      </span>
+
+      <a
+        href="#"
+        phx-click="show-tooltip"
+        phx-click-away="hide-tooltip"
+        phx-value-paddle-product-id={@paddle_product_id}
+        class="flex justify-center align-items-center"
+      >
+        <%= @disabled_message %>
+        <Heroicons.information_circle class="w-5 h-5 ml-2" />
+      </a>
+    </div>
+    """
+  end
+
+  defp usage_within_plan_limits?(%{available: false}) do
+    {:error, :plan_unavailable}
+  end
+
+  defp usage_within_plan_limits?(%{
+         available: true,
+         usage: usage,
+         user: user,
+         plan_to_render: plan
+       }) do
     # At this point, the user is *not guaranteed* to have a `trial_expiry_date`,
     # because in the past we've let users upgrade without that constraint, as
     # well as transfer sites to those accounts. to these accounts we won't be
@@ -232,9 +299,15 @@ defmodule PlausibleWeb.Components.Billing.PlanBox do
           []
       end
 
-    Quota.ensure_within_plan_limits(usage, plan, limit_checking_opts) == :ok
+    Quota.ensure_within_plan_limits(usage, plan, limit_checking_opts)
   end
 
+  defp limits({:error, {:over_plan_limits, limits}}) do
+    limits
+  end
+
+  defp limits(_), do: nil
+
   defp get_paddle_product_id(%Plan{monthly_product_id: plan_id}, :monthly), do: plan_id
   defp get_paddle_product_id(%Plan{yearly_product_id: plan_id}, :yearly), do: plan_id
 
diff --git a/lib/plausible_web/live/choose_plan.ex b/lib/plausible_web/live/choose_plan.ex
index 39d2866afead..671a3e32a715 100644
--- a/lib/plausible_web/live/choose_plan.ex
+++ b/lib/plausible_web/live/choose_plan.ex
@@ -189,6 +189,14 @@ defmodule PlausibleWeb.Live.ChoosePlan do
      )}
   end
 
+  def handle_event("show-tooltip", %{"paddle-product-id" => product_id}, socket) do
+    {:noreply, assign(socket, display_tooltip_product_id: product_id)}
+  end
+
+  def handle_event("hide-tooltip", _, socket) do
+    {:noreply, assign(socket, display_tooltip_product_id: nil)}
+  end
+
   defp default_selected_volume(%Plan{monthly_pageview_limit: limit}, _, _), do: limit
 
   defp default_selected_volume(_, last_30_days_usage, available_volumes) do
diff --git a/test/plausible_web/live/choose_plan_test.exs b/test/plausible_web/live/choose_plan_test.exs
index a463cdbdcab1..7df389c1ac70 100644
--- a/test/plausible_web/live/choose_plan_test.exs
+++ b/test/plausible_web/live/choose_plan_test.exs
@@ -19,6 +19,8 @@ defmodule PlausibleWeb.Live.ChoosePlanTest do
   @slider_value "#slider-value"
 
   @growth_plan_box "#growth-plan-box"
+  @growth_plan_tooltip "#growth-plan-box .tooltip-wrapper span"
+  @growth_plan_tooltip_link ~s/#growth-plan-box .tooltip-wrapper a[phx-click="show-tooltip"]/
   @growth_price_tag_amount "#growth-price-tag-amount"
   @growth_price_tag_interval "#growth-price-tag-interval"
   @growth_highlight_pill "#{@growth_plan_box} #highlight-pill"
@@ -243,6 +245,7 @@ defmodule PlausibleWeb.Live.ChoosePlanTest do
 
       refute class_of_element(doc, @growth_checkout_button) =~ "pointer-events-none"
       refute class_of_element(doc, @business_checkout_button) =~ "pointer-events-none"
+      refute element_exists?(doc, @growth_plan_tooltip)
 
       generate_usage_for(site, 1)
 
@@ -251,6 +254,9 @@ defmodule PlausibleWeb.Live.ChoosePlanTest do
 
       assert class_of_element(doc, @growth_checkout_button) =~ "pointer-events-none"
       assert class_of_element(doc, @business_checkout_button) =~ "pointer-events-none"
+
+      assert text_of_element(doc, @growth_plan_tooltip) ==
+               "Your usage exceeds the following limit(s): Monthly pageview limit"
     end
 
     test "allows upgrade to a 10k plan with a pageview allowance margin of 0.3 when trial ended 10 days ago",
@@ -497,6 +503,9 @@ defmodule PlausibleWeb.Live.ChoosePlanTest do
 
       assert text_of_element(doc, @growth_plan_box) =~ "Your usage exceeds this plan"
       assert class_of_element(doc, @growth_checkout_button) =~ "pointer-events-none"
+
+      assert text_of_element(doc, @growth_plan_tooltip) ==
+               "Your usage exceeds the following limit(s): Team member limit"
     end
 
     test "checkout is disabled when sites usage exceeds rendered plan limit", %{
@@ -509,6 +518,55 @@ defmodule PlausibleWeb.Live.ChoosePlanTest do
 
       assert text_of_element(doc, @growth_plan_box) =~ "Your usage exceeds this plan"
       assert class_of_element(doc, @growth_checkout_button) =~ "pointer-events-none"
+
+      assert text_of_element(doc, @growth_plan_tooltip) ==
+               "Your usage exceeds the following limit(s): Site limit"
+    end
+
+    test "clicking the tooltip changes makes it sticky", %{
+      conn: conn,
+      user: user
+    } do
+      insert(:site,
+        memberships: [
+          build(:site_membership, user: user, role: :owner),
+          build(:site_membership, user: build(:user)),
+          build(:site_membership, user: build(:user)),
+          build(:site_membership, user: build(:user)),
+          build(:site_membership, user: build(:user))
+        ]
+      )
+
+      {:ok, lv, doc} = get_liveview(conn)
+
+      assert class_of_element(doc, @growth_plan_tooltip) =~ "opacity-0 group-hover:opacity-90"
+
+      doc = element(lv, @growth_plan_tooltip_link) |> render_click()
+
+      assert class_of_element(doc, @growth_plan_tooltip) =~ "opacity-90"
+      refute class_of_element(doc, @growth_plan_tooltip) =~ "opacity-0"
+    end
+
+    test "when more than one limit is exceeded, the tooltip enumerates them", %{
+      conn: conn,
+      user: user
+    } do
+      for _ <- 1..11, do: insert(:site, members: [user])
+
+      insert(:site,
+        memberships: [
+          build(:site_membership, user: user, role: :owner),
+          build(:site_membership, user: build(:user)),
+          build(:site_membership, user: build(:user)),
+          build(:site_membership, user: build(:user)),
+          build(:site_membership, user: build(:user))
+        ]
+      )
+
+      {:ok, _lv, doc} = get_liveview(conn)
+
+      assert text_of_element(doc, @growth_plan_tooltip) =~ "Team member limit"
+      assert text_of_element(doc, @growth_plan_tooltip) =~ "Site limit"
     end
 
     test "checkout is not disabled when pageview usage exceeded but next upgrade allowed by override",