diff --git a/lib/frenzy/network.ex b/lib/frenzy/network.ex
index 9c8f756..616c88e 100644
--- a/lib/frenzy/network.ex
+++ b/lib/frenzy/network.ex
@@ -23,6 +23,10 @@ defmodule Frenzy.Network do
 
   @spec http_get(String.t()) :: Tesla.Env.result()
   def http_get(url) do
+    if Frenzy.sentry_enabled?() do
+      Sentry.Context.add_breadcrumb(%{category: "http_get", message: url})
+    end
+
     HTTP.get(url)
   end
 
@@ -77,6 +81,10 @@ defmodule Frenzy.Network do
   @spec gemini_request(String.t() | URI.t()) :: {:ok, Gemini.Response.t()} | {:error, term()}
 
   def gemini_request(uri) do
+    if Frenzy.sentry_enabled?() do
+      Sentry.Context.add_breadcrumb(%{category: "gemini_request", message: uri})
+    end
+
     case Gemini.request(uri) do
       {:ok, %Gemini.Response{status: code} = response} when code in @gemini_success_codes ->
         {:ok, response}
diff --git a/lib/frenzy/task/create_item.ex b/lib/frenzy/task/create_item.ex
index 2020df5..c71f0e2 100644
--- a/lib/frenzy/task/create_item.ex
+++ b/lib/frenzy/task/create_item.ex
@@ -47,6 +47,13 @@ defmodule Frenzy.Task.CreateItem do
         feed.pipeline.stages
         |> Enum.reduce({:ok, item_params}, fn
           stage, {:ok, item_params} ->
+            if Frenzy.sentry_enabled?() do
+              Sentry.Context.add_breadcrumb(%{
+                category: "pipeline",
+                message: stage["module_name"]
+              })
+            end
+
             apply(String.to_existing_atom("Elixir." <> stage["module_name"]), :apply, [
               stage["options"],
               item_params
@@ -69,8 +76,12 @@ defmodule Frenzy.Task.CreateItem do
 
           if Frenzy.sentry_enabled?() do
             Sentry.capture_message(
-              "Error evaluating pipeline '#{feed.pipeline.name}': #{inspect(error)}",
-              extra: %{feed_id: feed.id, pipeline_id: feed.pipeline.id}
+              "Error evaluating pipeline: #{inspect(error)}",
+              extra: %{
+                feed_id: feed.id,
+                pipeline_id: feed.pipeline.id,
+                pipeline_name: feed.pipeline.name
+              }
             )
           end
 
@@ -106,8 +117,12 @@ defmodule Frenzy.Task.CreateItem do
                 Logger.error(changeset.errors)
 
                 if Frenzy.sentry_enabled?() do
-                  Sentry.capture_message("Error inserting item '#{item_params.guid}'",
-                    extra: %{feed_id: feed.id, errors: changeset.errors}
+                  Sentry.capture_message("Error inserting item: #{inspect(changeset.errors)}",
+                    extra: %{
+                      item_guid: item_params.guid,
+                      feed_id: feed.id,
+                      errors: changeset.errors
+                    }
                   )
                 end
             end
diff --git a/lib/frenzy/update_feeds.ex b/lib/frenzy/update_feeds.ex
index a5af87a..2f71087 100644
--- a/lib/frenzy/update_feeds.ex
+++ b/lib/frenzy/update_feeds.ex
@@ -151,8 +151,8 @@ defmodule Frenzy.UpdateFeeds do
         Logger.error("Couldn't load feed #{feed.feed_url}: #{inspect(reason)}")
 
         if Frenzy.sentry_enabled?() do
-          Sentry.capture_message("Error loading HTTP feed '#{feed.feed_url}': #{inspect(reason)}",
-            extra: %{feed_id: feed.id}
+          Sentry.capture_message("Error loading HTTP feed: #{inspect(reason)}",
+            extra: %{feed_id: feed.id, feed_url: feed.feed_url}
           )
         end
     end
@@ -168,8 +168,8 @@ defmodule Frenzy.UpdateFeeds do
 
         if Frenzy.sentry_enabled?() do
           Sentry.capture_message(
-            "Error loading Gemini feed '#{feed.feed_url}': #{inspect(reason)}",
-            extra: %{feed_id: feed.id}
+            "Error loading Gemini feed: #{inspect(reason)}",
+            extra: %{feed_id: feed.id, feed_url: feed.feed_url}
           )
         end
     end
@@ -184,8 +184,8 @@ defmodule Frenzy.UpdateFeeds do
         Logger.error("Unable to parse feed at '#{feed.feed_url}': #{inspect(reason)}")
 
         if Frenzy.sentry_enabled?() do
-          Sentry.capture_message("Unable to parse feed '#{feed.feed_url}': #{inspect(reason)}",
-            extra: %{feed_id: feed.id}
+          Sentry.capture_message("Unable to parse feed: #{inspect(reason)}",
+            extra: %{feed_id: feed.id, feed_url: feed.feed_url}
           )
         end
     end