diff --git a/app/web/errors/error_classifier.rb b/app/web/errors/error_classifier.rb
index 9776a1f1..b8b42e40 100644
--- a/app/web/errors/error_classifier.rb
+++ b/app/web/errors/error_classifier.rb
@@ -19,10 +19,23 @@ module ErrorClassifier # rubocop:disable Metrics/ModuleLength -- Decision catalo
       # Immutable HTTP decision for a classified error.
       Decision = Data.define(
         :status, :code, :message, :kind, :cacheable, :retryable, :next_action, :retry_action
-      )
+      ) do
+        # Maps <500 classified decisions to their empty RenderResult reason.
+        #
+        # @return [String]
+        def empty_reason
+          case code
+          when BLOCKED_SURFACE_CODE then 'blocked_surface'
+          when 'FORBIDDEN' then 'forbidden'
+          else 'content_extraction_empty'
+          end
+        end
+      end
 
       ##
       # Gem strategy attempts plus expanded transport telemetry for feed Observability / headers.
+      TRANSPORT_KEYS = %i[request_id strategy_used render_ms error_category timeout_phase].freeze
+
       Diagnostics = Data.define(
         :strategy_attempts, :request_id, :strategy_used, :render_ms, :error_category, :timeout_phase,
         :surface_category
@@ -39,14 +52,15 @@ def empty
           #
           # @param error [Exception, nil]
           # @return [Html2rss::Web::ErrorClassifier::Diagnostics]
-          def from_error(error) # rubocop:disable Metrics/AbcSize -- chain dig + surface_category
+          def from_error(error) # rubocop:disable Metrics/AbcSize, Metrics/CyclomaticComplexity, Metrics/MethodLength, Metrics/PerceivedComplexity -- chain dig
             carried = decided_diagnostics(error)
             return carried if carried
 
             chain = ErrorClassifier.error_chain(error)
-            with_attempts = chain.find { it.is_a?(::Html2rss::NoFeedItemsExtracted) }
+            with_attempts = chain.find { it.is_a?(::Html2rss::Error) && Array(it.attempts).any? }
+            meta_error = chain.find { it.is_a?(::Html2rss::Error) && it.transport_meta&.any? }
             list = with_attempts ? Array(with_attempts.attempts) : []
-            fields = transport_fields(list)
+            fields = transport_fields(list, fallback_meta: meta_error&.transport_meta)
             fields[:timeout_phase] ||= timeout_phase_from_chain(chain)
             fields[:surface_category] = surface_category_from_chain(chain)
 
@@ -78,16 +92,11 @@ def decided_diagnostics(error)
           end
 
           # @param attempts [Array<Hash>]
+          # @param fallback_meta [Hash, nil]
           # @return [Hash{Symbol=>Object}]
-          def transport_fields(attempts)
-            meta = attempts.filter_map { it[:transport_meta] || it['transport_meta'] }.last
-            {
-              request_id: dig_meta(meta, :request_id),
-              strategy_used: dig_meta(meta, :strategy_used),
-              render_ms: dig_meta(meta, :render_ms),
-              error_category: dig_meta(meta, :error_category),
-              timeout_phase: dig_meta(meta, :timeout_phase)
-            }
+          def transport_fields(attempts, fallback_meta: nil)
+            meta = attempts.filter_map { it[:transport_meta] || it['transport_meta'] }.last || fallback_meta
+            TRANSPORT_KEYS.to_h { [it, dig_meta(meta, it)] }
           end
 
           # @param chain [Array<Exception>]
@@ -116,12 +125,7 @@ def dig_meta(meta, key)
         #
         # @return [Hash{Symbol=>Object}]
         def to_h
-          details = strategy_attempts.empty? ? {} : { strategy_attempts: strategy_attempts }
-          %i[request_id strategy_used render_ms error_category timeout_phase surface_category].each do |key|
-            val = public_send(key)
-            details[key] = val if val
-          end
-          details
+          super.reject { |_, val| val.nil? || val == [] }
         end
       end
       EMPTY_DIAGNOSTICS = Diagnostics.new(
@@ -159,7 +163,12 @@ def initialize(decision, diagnostics: Diagnostics.empty)
       # Non-timeout transport failures → internal network decision when unclassified.
       NETWORK_ERRORS = [
         SocketError, EOFError, Errno::ECONNREFUSED, Errno::EHOSTUNREACH,
-        HTTPX::ConnectionError, HTTPX::TLSError
+        HTTPX::ConnectionError, HTTPX::TLSError,
+        *(if ::Html2rss::RequestService.const_defined?(:ConnectionFailed, false)
+            [::Html2rss::RequestService::ConnectionFailed]
+          else
+            []
+          end)
       ].freeze
 
       AUTH_META = { kind: 'auth', retryable: false, next_action: 'enter_token', retry_action: 'none' }.freeze
@@ -175,11 +184,8 @@ def initialize(decision, diagnostics: Diagnostics.empty)
         status: 422,
         code: EXTRACTION_EMPTY_CODE,
         message: EXTRACTION_EMPTY_MESSAGE,
-        kind: 'input',
         cacheable: true,
-        retryable: false,
-        next_action: 'correct_input',
-        retry_action: 'none'
+        **INPUT_META
       ).freeze
 
       # Shell / high-entropy empties stay a plain 422 but must not be stored.
@@ -191,15 +197,11 @@ def initialize(decision, diagnostics: Diagnostics.empty)
       BLOCKED_SURFACE_CODE = 'BLOCKED_SURFACE'
       BLOCKED_SURFACE_MESSAGE = 'This site blocked automated access. Try another URL or site.'
 
+      # Anti-bot challenge surfaces deterministically block automated fetches for this IP;
+      # cacheable: true avoids hammering challenge endpoints during the feed TTL.
       BLOCKED_SURFACE = Decision.new(
-        status: 422,
-        code: BLOCKED_SURFACE_CODE,
-        message: BLOCKED_SURFACE_MESSAGE,
-        kind: 'input',
-        cacheable: true,
-        retryable: false,
-        next_action: 'correct_input',
-        retry_action: 'none'
+        status: 422, code: BLOCKED_SURFACE_CODE, message: BLOCKED_SURFACE_MESSAGE,
+        cacheable: true, **INPUT_META
       ).freeze
 
       SCRAPER_UNAVAILABLE_CODE = 'SCRAPER_UNAVAILABLE'
@@ -211,9 +213,7 @@ def initialize(decision, diagnostics: Diagnostics.empty)
         message: SCRAPER_UNAVAILABLE_MESSAGE,
         kind: 'server',
         cacheable: false,
-        retryable: true,
-        next_action: 'retry',
-        retry_action: 'primary'
+        **RETRY_META
       ).freeze
 
       SERVICE_UNAVAILABLE = Decision.new(
@@ -222,9 +222,7 @@ def initialize(decision, diagnostics: Diagnostics.empty)
         message: 'The server is too busy or the request timed out.',
         kind: 'server',
         cacheable: false,
-        retryable: true,
-        next_action: 'retry',
-        retry_action: 'primary'
+        **RETRY_META
       ).freeze
 
       GATEWAY_TIMEOUT = Decision.new(
@@ -233,9 +231,7 @@ def initialize(decision, diagnostics: Diagnostics.empty)
         message: 'The target website took too long to respond.',
         kind: 'network',
         cacheable: false,
-        retryable: true,
-        next_action: 'retry',
-        retry_action: 'primary'
+        **RETRY_META
       ).freeze
 
       INTERNAL_SERVER_ERROR = Decision.new(
@@ -244,20 +240,15 @@ def initialize(decision, diagnostics: Diagnostics.empty)
         message: 'Internal Server Error',
         kind: 'server',
         cacheable: false,
-        retryable: true,
-        next_action: 'retry',
-        retry_action: 'primary'
+        **RETRY_META
       ).freeze
 
       PRIVATE_NETWORK_DENIED = Decision.new(
         status: 403,
         code: 'FORBIDDEN',
         message: 'Requests to private or loopback networks are forbidden.',
-        kind: 'input',
         cacheable: true,
-        retryable: false,
-        next_action: 'correct_input',
-        retry_action: 'none'
+        **INPUT_META
       ).freeze
 
       INTERNAL_NETWORK_ERROR = Decision.new(
@@ -266,9 +257,7 @@ def initialize(decision, diagnostics: Diagnostics.empty)
         message: 'Internal Server Error',
         kind: 'network',
         cacheable: false,
-        retryable: true,
-        next_action: 'retry',
-        retry_action: 'primary'
+        **RETRY_META
       ).freeze
 
       class << self
diff --git a/app/web/feeds/contracts.rb b/app/web/feeds/contracts.rb
index 2caf22d1..5573b388 100644
--- a/app/web/feeds/contracts.rb
+++ b/app/web/feeds/contracts.rb
@@ -103,6 +103,11 @@ def http_status
           def client_message
             decision.message
           end
+
+          # @return [Boolean]
+          def cacheable?
+            decision.nil? || decision.cacheable
+          end
         end
       end
     end
diff --git a/app/web/feeds/renderer.rb b/app/web/feeds/renderer.rb
index 35034821..97ea599b 100644
--- a/app/web/feeds/renderer.rb
+++ b/app/web/feeds/renderer.rb
@@ -143,7 +143,7 @@ def plain_response?(result)
           # @param result [Html2rss::Web::Feeds::Contracts::RenderResult]
           # @return [void]
           def apply_cache_headers(response, result)
-            return expires_now(response) unless result.decision.nil? || result.decision.cacheable
+            return expires_now(response) unless result.cacheable?
 
             expires(response, result.ttl_seconds, cache_control: 'public')
           end
diff --git a/app/web/feeds/service.rb b/app/web/feeds/service.rb
index 217a9398..6294434c 100644
--- a/app/web/feeds/service.rb
+++ b/app/web/feeds/service.rb
@@ -7,10 +7,6 @@ module Feeds
       # Shared synchronous feed service around the html2rss gem.
       module Service
         class << self
-          EMPTY_REASON_BY_CODE = {
-            ErrorClassifier::BLOCKED_SURFACE_CODE => 'blocked_surface',
-            'FORBIDDEN' => 'forbidden'
-          }.freeze
           # @param resolved_source [Html2rss::Web::Feeds::Contracts::ResolvedSource]
           # @return [Html2rss::Web::Feeds::Contracts::RenderResult]
           def call(resolved_source)
@@ -19,7 +15,7 @@ def call(resolved_source)
             Cache.fetch(
               cache_key,
               ttl_seconds: resolved_source.ttl_seconds,
-              cacheable: ->(result) { result.decision.nil? || result.decision.cacheable }
+              cacheable: lambda(&:cacheable?)
             ) do
               build_result(resolved_source, cache_key)
             end
@@ -116,7 +112,7 @@ def classified_empty_result(error, decision, diagnostics, resolved_source, cache
               cache_key:,
               error_message: error.message,
               error_class: error.class.name,
-              empty_reason: EMPTY_REASON_BY_CODE.fetch(decision.code, 'content_extraction_empty')
+              empty_reason: decision.empty_reason
             )
           end
 
diff --git a/docs/README.md b/docs/README.md
index 7ac688af..e238b392 100644
--- a/docs/README.md
+++ b/docs/README.md
@@ -265,7 +265,7 @@ Start from the newest `feed.create`, `feed.render`, and `request.error` lines. F
 3. **Decision tree**
    - `SCRAPER_UNAVAILABLE` → scraper down or unreachable
    - `SERVICE_UNAVAILABLE` with queue/boot timeout wording in `details.error_message` → our capacity or Chromium boot, not the target site
-   - `BLOCKED_SURFACE` → site blocked automation (product signal)
+   - `BLOCKED_SURFACE` → site blocked automation (product signal; cached for feed TTL with `details.cacheable=true` to avoid hammering challenge pages)
    - `EXTRACTION_EMPTY` → selectors/config (product signal)
    - `GATEWAY_TIMEOUT` → slow or hostile target, or timeout ladder mismatch (see **Compose timeout ladder**)
 
diff --git a/spec/html2rss/web/error_classifier_spec.rb b/spec/html2rss/web/error_classifier_spec.rb
index bc15cbc7..c94dcdbb 100644
--- a/spec/html2rss/web/error_classifier_spec.rb
+++ b/spec/html2rss/web/error_classifier_spec.rb
@@ -81,6 +81,21 @@
       expect(described_class.classify(error)).to eq(described_class::BLOCKED_SURFACE)
     end
 
+    it 'exposes blocked-surface cache policy and empty reason', :aggregate_failures do
+      expect(described_class::BLOCKED_SURFACE.cacheable).to be(true)
+      expect(described_class::BLOCKED_SURFACE.empty_reason).to eq('blocked_surface')
+    end
+
+    it 'classifies ConnectionFailed as internal network error', :aggregate_failures,
+       if: Html2rss::RequestService.const_defined?(:ConnectionFailed, false) do
+      expect(described_class.classify(Html2rss::RequestService::ConnectionFailed.new('refused'))).to eq(
+        described_class::INTERNAL_NETWORK_ERROR
+      )
+      expect(described_class.classify(Html2rss::RequestService::ConnectionFailed.new('refused'))).to have_attributes(
+        status: 500, kind: 'network', cacheable: false
+      )
+    end
+
     it 'uses one human sentence for classified user decisions', :aggregate_failures do
       expect(described_class::BLOCKED_SURFACE.message).to eq(
         'This site blocked automated access. Try another URL or site.'
@@ -304,6 +319,43 @@
 
       expect(described_class::Diagnostics.from_error(decided)).to eq(carried)
     end
+
+    it 'extracts attempts from RequestTimedOut on the chain', :aggregate_failures do
+      attempts = [{ strategy: :default, error_class: 'Html2rss::RequestService::RequestTimedOut', elapsed_ms: 12 }]
+      error = Html2rss::RequestService::RequestTimedOut.new('timed out', timeout_phase: 'work')
+      error.attempts = attempts
+
+      diagnostics = described_class::Diagnostics.from_error(error)
+      expect(diagnostics.strategy_attempts).to eq(attempts)
+      expect(diagnostics.timeout_phase).to eq('work')
+    end
+
+    it 'extracts attempts from BlockedSurfaceDetected on the chain', :aggregate_failures do
+      attempts = [{ strategy: :botasaurus, error_class: 'Html2rss::RequestService::BlockedSurfaceDetected' }]
+      error = Html2rss::RequestService::BlockedSurfaceDetected.new('challenge')
+      error.attempts = attempts
+
+      expect(described_class::Diagnostics.from_error(error).strategy_attempts).to eq(attempts)
+    end
+
+    it 'extracts attempts from ConnectionFailed on the chain', :aggregate_failures,
+       if: Html2rss::RequestService.const_defined?(:ConnectionFailed, false) do
+      attempts = [{ strategy: :default, error_class: 'Html2rss::RequestService::ConnectionFailed' }]
+      error = Html2rss::RequestService::ConnectionFailed.new('refused')
+      error.attempts = attempts
+
+      expect(described_class::Diagnostics.from_error(error).strategy_attempts).to eq(attempts)
+    end
+
+    it 'extracts transport_meta without attempts from Html2rss::Error on the chain', :aggregate_failures do
+      error = Html2rss::RequestService::RequestTimedOut.new('queued', timeout_phase: 'queue')
+      error.transport_meta = { request_id: 'req-direct', render_ms: 99, strategy_used: 'botasaurus' }
+
+      expect(described_class::Diagnostics.from_error(error)).to have_attributes(
+        request_id: 'req-direct', render_ms: 99, strategy_used: 'botasaurus', timeout_phase: 'queue'
+      )
+      expect(described_class::Diagnostics.from_error(error).strategy_attempts).to eq([])
+    end
   end
 
   describe '.error_chain' do
diff --git a/spec/html2rss/web/feeds/responder_spec.rb b/spec/html2rss/web/feeds/responder_spec.rb
index b9a1f98c..fcc9efd3 100644
--- a/spec/html2rss/web/feeds/responder_spec.rb
+++ b/spec/html2rss/web/feeds/responder_spec.rb
@@ -218,6 +218,35 @@
       expect(body).to eq(Html2rss::Web::ErrorClassifier::EXTRACTION_EMPTY_MESSAGE)
     end
 
+    it 'emits blocked surface empty with cacheable telemetry', :aggregate_failures do # rubocop:disable RSpec/ExampleLength
+      blocked = Html2rss::Web::Feeds::Contracts::RenderResult.new(
+        status: :empty,
+        payload: Html2rss::Web::Feeds::Contracts::RenderPayload.new(
+          feed: nil,
+          site_title: 'https://example.com',
+          url: 'https://example.com'
+        ),
+        ttl_seconds: 600,
+        cache_key: 'feed_result:blocked',
+        decision: Html2rss::Web::ErrorClassifier::BLOCKED_SURFACE,
+        empty_reason: 'blocked_surface'
+      )
+      allow(Html2rss::Web::Feeds::Service).to receive(:call).and_return(blocked)
+
+      write_response
+
+      expect(Html2rss::Web::Observability).to have_received(:emit).with(
+        event_name: 'feed.render',
+        outcome: 'failure',
+        details: include(
+          error_code: 'BLOCKED_SURFACE',
+          reason: 'blocked_surface',
+          cacheable: true
+        ),
+        level: :warn
+      )
+    end
+
     it 'emits empty extraction as a failure outcome' do # rubocop:disable RSpec/ExampleLength
       write_response
 
diff --git a/spec/html2rss/web/feeds/service_spec.rb b/spec/html2rss/web/feeds/service_spec.rb
index e855af67..d03915cb 100644
--- a/spec/html2rss/web/feeds/service_spec.rb
+++ b/spec/html2rss/web/feeds/service_spec.rb
@@ -316,6 +316,30 @@ def expected_payload
       expect(result.status).to eq(:empty)
       expect(result.empty_reason).to eq('blocked_surface')
       expect(result.decision).to eq(Html2rss::Web::ErrorClassifier::BLOCKED_SURFACE)
+      expect(result.cacheable?).to be(true)
+
+      described_class.call(resolved_source)
+      described_class.call(resolved_source)
+
+      expect(Html2rss).to have_received(:feed_result).once
+    end
+  end
+
+  context 'when RequestTimedOut carries attempt diagnostics' do
+    let(:attempts) do
+      [{ strategy: :default, error_class: 'Html2rss::RequestService::RequestTimedOut', elapsed_ms: 500 }]
+    end
+
+    before do
+      error = Html2rss::RequestService::RequestTimedOut.new('timed out', timeout_phase: 'work')
+      error.attempts = attempts
+      allow(Html2rss).to receive(:feed_result).with(resolved_source.generator_input).and_raise(error)
+    end
+
+    it 'preserves strategy_attempts on the error RenderResult', :aggregate_failures do
+      expect(result.status).to eq(:error)
+      expect(result.decision).to eq(Html2rss::Web::ErrorClassifier::GATEWAY_TIMEOUT)
+      expect(result.diagnostics.strategy_attempts).to eq(attempts)
     end
   end