diff --git a/app/controllers/api/v1/widget/contacts_controller.rb b/app/controllers/api/v1/widget/contacts_controller.rb
index 5138fe675..6c595ab59 100644
--- a/app/controllers/api/v1/widget/contacts_controller.rb
+++ b/app/controllers/api/v1/widget/contacts_controller.rb
@@ -19,7 +19,7 @@ class Api::V1::Widget::ContactsController < Api::V1::Widget::BaseController
       contact = @contact
     end
 
-    @contact_inbox.update(hmac_verified: true) if should_verify_hmac? && valid_hmac?
+    @contact_inbox.update(hmac_verified: true) if should_verify_hmac?
 
     identify_contact(contact)
   end
diff --git a/app/javascript/dashboard/components-next/HelpCenter/EmptyState/Portal/PortalEmptyState.vue b/app/javascript/dashboard/components-next/HelpCenter/EmptyState/Portal/PortalEmptyState.vue
index b7a986254..192e1d5ee 100644
--- a/app/javascript/dashboard/components-next/HelpCenter/EmptyState/Portal/PortalEmptyState.vue
+++ b/app/javascript/dashboard/components-next/HelpCenter/EmptyState/Portal/PortalEmptyState.vue
@@ -26,6 +26,7 @@ const onPortalCreate = ({ slug: portalSlug, locale }) => {
   <EmptyStateLayout
     :title="$t('HELP_CENTER.TITLE')"
     :subtitle="$t('HELP_CENTER.NEW_PAGE.DESCRIPTION')"
+    class="bg-n-surface-1"
   >
     <template #empty-state-item>
       <div class="grid grid-cols-2 gap-4 p-px">
diff --git a/app/models/account.rb b/app/models/account.rb
index 85754a395..06f47636e 100644
--- a/app/models/account.rb
+++ b/app/models/account.rb
@@ -41,7 +41,7 @@ class Account < ApplicationRecord
         'audio_transcriptions': { 'type': %w[boolean null] },
         'auto_resolve_label': { 'type': %w[string null] },
         'keep_pending_on_bot_failure': { 'type': %w[boolean null] },
-        'captain_disable_auto_resolve': { 'type': %w[boolean null] },
+        'captain_auto_resolve_mode': { 'type': %w[string null], 'enum': ['evaluated', 'legacy', 'disabled', nil] },
         'conversation_required_attributes': {
           'type': %w[array null],
           'items': { 'type': 'string' }
@@ -93,7 +93,8 @@ class Account < ApplicationRecord
   store_accessor :settings, :captain_models, :captain_features
   store_accessor :settings, :reporting_timezone
   store_accessor :settings, :keep_pending_on_bot_failure
-  store_accessor :settings, :captain_disable_auto_resolve
+  store_accessor :settings, :captain_auto_resolve_mode
+  include AccountCaptainAutoResolve
 
   has_many :account_users, dependent: :destroy_async
   has_many :agent_bot_inboxes, dependent: :destroy_async
diff --git a/app/models/concerns/account_captain_auto_resolve.rb b/app/models/concerns/account_captain_auto_resolve.rb
new file mode 100644
index 000000000..5d17e92f9
--- /dev/null
+++ b/app/models/concerns/account_captain_auto_resolve.rb
@@ -0,0 +1,21 @@
+module AccountCaptainAutoResolve
+  extend ActiveSupport::Concern
+
+  VALID_CAPTAIN_AUTO_RESOLVE_MODES = %w[evaluated legacy disabled].freeze
+
+  included do
+    VALID_CAPTAIN_AUTO_RESOLVE_MODES.each do |mode|
+      define_method("captain_auto_resolve_#{mode}?") do
+        captain_auto_resolve_mode == mode
+      end
+    end
+  end
+
+  def captain_auto_resolve_mode
+    mode = settings&.[]('captain_auto_resolve_mode')
+    return mode if VALID_CAPTAIN_AUTO_RESOLVE_MODES.include?(mode)
+    return 'disabled' if settings&.[]('captain_disable_auto_resolve') == true
+
+    feature_enabled?('captain_tasks') ? 'evaluated' : 'legacy'
+  end
+end
diff --git a/config/markdown_embeds.yml b/config/markdown_embeds.yml
index f85e181e3..b826931ec 100644
--- a/config/markdown_embeds.yml
+++ b/config/markdown_embeds.yml
@@ -104,11 +104,11 @@ wistia:
     </div>
 
 bunny:
-  regex: 'https?://iframe\.mediadelivery\.net/play/(?<library_id>\d+)/(?<video_id>[^&/?]+)'
+  regex: 'https?://(?:iframe|player)\.mediadelivery\.net/(?:play|embed)/(?<library_id>\d+)/(?<video_id>[^&/?]+)'
   template: |
     <div style="position: relative; padding-top: 56.25%;">
       <iframe
-        src="https://iframe.mediadelivery.net/embed/%{library_id}/%{video_id}?autoplay=false&loop=false&muted=false&preload=true&responsive=true"
+        src="https://player.mediadelivery.net/embed/%{library_id}/%{video_id}?autoplay=false&loop=false&muted=false&preload=true&responsive=true"
         title="Bunny video player"
         loading="lazy"
         style="border: 0; position: absolute; top: 0; height: 100%; width: 100%;"
diff --git a/enterprise/app/jobs/captain/inbox_pending_conversations_resolution_job.rb b/enterprise/app/jobs/captain/inbox_pending_conversations_resolution_job.rb
index 538c03d22..0be179f04 100644
--- a/enterprise/app/jobs/captain/inbox_pending_conversations_resolution_job.rb
+++ b/enterprise/app/jobs/captain/inbox_pending_conversations_resolution_job.rb
@@ -5,9 +5,9 @@ class Captain::InboxPendingConversationsResolutionJob < ApplicationJob
   queue_as :low
 
   def perform(inbox)
-    return if inbox.account.captain_disable_auto_resolve
+    return if inbox.account.captain_auto_resolve_disabled?
 
-    if inbox.account.feature_enabled?('captain_tasks')
+    if evaluate_conversation_completion?(inbox.account)
       perform_with_evaluation(inbox)
     else
       perform_time_based(inbox)
@@ -18,6 +18,10 @@ class Captain::InboxPendingConversationsResolutionJob < ApplicationJob
 
   private
 
+  def evaluate_conversation_completion?(account)
+    account.feature_enabled?('captain_tasks') && account.captain_auto_resolve_evaluated?
+  end
+
   def perform_time_based(inbox)
     Current.executed_by = inbox.captain_assistant
 
diff --git a/enterprise/app/jobs/enterprise/account/conversations_resolution_scheduler_job.rb b/enterprise/app/jobs/enterprise/account/conversations_resolution_scheduler_job.rb
index 8b6527c93..7ccebf72f 100644
--- a/enterprise/app/jobs/enterprise/account/conversations_resolution_scheduler_job.rb
+++ b/enterprise/app/jobs/enterprise/account/conversations_resolution_scheduler_job.rb
@@ -12,7 +12,7 @@ module Enterprise::Account::ConversationsResolutionSchedulerJob
       inbox = captain_inbox.inbox
 
       next if inbox.email?
-      next if inbox.account.captain_disable_auto_resolve
+      next if inbox.account.captain_auto_resolve_disabled?
 
       Captain::InboxPendingConversationsResolutionJob.perform_later(
         inbox
diff --git a/enterprise/lib/captain/tools/resolve_conversation_tool.rb b/enterprise/lib/captain/tools/resolve_conversation_tool.rb
index 2b71098c9..eeffc3f06 100644
--- a/enterprise/lib/captain/tools/resolve_conversation_tool.rb
+++ b/enterprise/lib/captain/tools/resolve_conversation_tool.rb
@@ -6,7 +6,7 @@ class Captain::Tools::ResolveConversationTool < Captain::Tools::BasePublicTool
     conversation = find_conversation(tool_context.state)
     return 'Conversation not found' unless conversation
     return "Conversation ##{conversation.display_id} is already resolved" if conversation.resolved?
-    return 'Auto-resolve is disabled for this account' if conversation.account.captain_disable_auto_resolve
+    return 'Auto-resolve is disabled for this account' if conversation.account.captain_auto_resolve_disabled?
 
     log_tool_usage('resolve_conversation', { conversation_id: conversation.id, reason: reason })
 
diff --git a/package.json b/package.json
index 0f74d03f4..c25a1f61d 100644
--- a/package.json
+++ b/package.json
@@ -79,7 +79,7 @@
     "json-logic-js": "^2.0.5",
     "lettersanitizer": "^1.0.6",
     "libphonenumber-js": "^1.11.9",
-    "markdown-it": "^13.0.2",
+    "markdown-it": "^14.1.1",
     "markdown-it-link-attributes": "^4.0.1",
     "md5": "^2.3.0",
     "mitt": "^3.0.1",
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index abd4acdeb..f1a6c7604 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -160,8 +160,8 @@ importers:
         specifier: ^1.11.9
         version: 1.11.9
       markdown-it:
-        specifier: ^13.0.2
-        version: 13.0.2
+        specifier: ^14.1.1
+        version: 14.1.1
       markdown-it-link-attributes:
         specifier: ^4.0.1
         version: 4.0.1
@@ -2206,10 +2206,6 @@ packages:
   entities@2.1.0:
     resolution: {integrity: sha512-hCx1oky9PFrJ611mf0ifBLBRW8lUUVRlFolb5gWRfIELabBlbp9xZvrqZLZAs+NxFnbfQoeGd8wDkygjg7U85w==}
 
-  entities@3.0.1:
-    resolution: {integrity: sha512-WiyBqoomrwMdFG1e0kqvASYfnlb0lp8M5o5Fw2OFq1hNZxxcNk8Ik0Xm7LxzBhuidnZB/UtBqVCgUz3kBOP51Q==}
-    engines: {node: '>=0.12'}
-
   entities@4.5.0:
     resolution: {integrity: sha512-V0hjH4dGPh9Ao5p0MoRY6BVqtwCjhz6vI5LT8AJ55H+4g9/4vbHx1I54fS0XuclLhDHArPQCiMjDxjaL8fPxhw==}
     engines: {node: '>=0.12'}
@@ -3087,9 +3083,6 @@ packages:
   linkify-it@3.0.3:
     resolution: {integrity: sha512-ynTsyrFSdE5oZ/O9GEf00kPngmOfVwazR5GKDq6EYfhlpFug3J2zybX56a2PRRpc9P+FuSoGNAwjlbDs9jJBPQ==}
 
-  linkify-it@4.0.1:
-    resolution: {integrity: sha512-C7bfi1UZmoj8+PQx22XyeXCuBlokoyWQL5pWSP+EI6nzRylyThouddufc2c1NDIcP9k5agmN9fLpA7VNJfIiqw==}
-
   linkify-it@5.0.0:
     resolution: {integrity: sha512-5aHCbzQRADcdP+ATqnDuhhJ/MRIqDkZX5pyjFHRRysS8vZ5AbqGEoFIb6pYHPZ+L/OC2Lc+xT8uHVVR5CAK/wQ==}
 
@@ -3210,12 +3203,8 @@ packages:
     resolution: {integrity: sha512-TchMembfxfNVpHkbtriWltGWc+m3xszaRD0CZup7GFFhzIgQqxIfn3eGj1yZpfuflzPvfkt611B2Q/Bsk1YnGg==}
     hasBin: true
 
-  markdown-it@13.0.2:
-    resolution: {integrity: sha512-FtwnEuuK+2yVU7goGn/MJ0WBZMM9ZPgU9spqlFs7/A/pDIUNSOQZhUgOqYCficIuR2QaFnrt8LHqBWsbTAoI5w==}
-    hasBin: true
-
-  markdown-it@14.1.0:
-    resolution: {integrity: sha512-a54IwgWPaeBCAAsv13YgmALOF1elABB08FxO9i+r4VFk5Vl4pKokRPeX8u5TCgSsPi6ec1otfLjdOpVcgbpshg==}
+  markdown-it@14.1.1:
+    resolution: {integrity: sha512-BuU2qnTti9YKgK5N+IeMubp14ZUKUUw7yeJbkjtosvHiP0AZ5c8IAgEMk79D0eC8F23r4Ac/q8cAIFdm2FtyoA==}
     hasBin: true
 
   math-intrinsics@1.1.0:
@@ -6841,8 +6830,6 @@ snapshots:
 
   entities@2.1.0: {}
 
-  entities@3.0.1: {}
-
   entities@4.5.0: {}
 
   entities@6.0.1: {}
@@ -7950,10 +7937,6 @@ snapshots:
     dependencies:
       uc.micro: 1.0.6
 
-  linkify-it@4.0.1:
-    dependencies:
-      uc.micro: 1.0.6
-
   linkify-it@5.0.0:
     dependencies:
       uc.micro: 2.1.0
@@ -8091,15 +8074,7 @@ snapshots:
       mdurl: 1.0.1
       uc.micro: 1.0.6
 
-  markdown-it@13.0.2:
-    dependencies:
-      argparse: 2.0.1
-      entities: 3.0.1
-      linkify-it: 4.0.1
-      mdurl: 1.0.1
-      uc.micro: 1.0.6
-
-  markdown-it@14.1.0:
+  markdown-it@14.1.1:
     dependencies:
       argparse: 2.0.1
       entities: 4.5.0
@@ -8738,7 +8713,7 @@ snapshots:
 
   prosemirror-markdown@1.13.0:
     dependencies:
-      markdown-it: 14.1.0
+      markdown-it: 14.1.1
       prosemirror-model: 1.22.3
 
   prosemirror-menu@1.2.4:
diff --git a/spec/config/markdown_embeds_spec.rb b/spec/config/markdown_embeds_spec.rb
index 9e9e56898..f609ac113 100644
--- a/spec/config/markdown_embeds_spec.rb
+++ b/spec/config/markdown_embeds_spec.rb
@@ -63,7 +63,11 @@ describe 'Markdown Embeds Configuration' do
         'bunny' => [
           { url: 'https://iframe.mediadelivery.net/play/431789/1f105841-cad9-46fe-a70e-b7623c60797c',
             expected: { 'library_id' => '431789', 'video_id' => '1f105841-cad9-46fe-a70e-b7623c60797c' } },
-          { url: 'https://iframe.mediadelivery.net/play/12345/abcdef-ghijkl', expected: { 'library_id' => '12345', 'video_id' => 'abcdef-ghijkl' } }
+          { url: 'https://iframe.mediadelivery.net/play/12345/abcdef-ghijkl', expected: { 'library_id' => '12345', 'video_id' => 'abcdef-ghijkl' } },
+          { url: 'https://player.mediadelivery.net/play/431789/1f105841-cad9-46fe-a70e-b7623c60797c',
+            expected: { 'library_id' => '431789', 'video_id' => '1f105841-cad9-46fe-a70e-b7623c60797c' } },
+          { url: 'https://iframe.mediadelivery.net/embed/256380/d9d9ab1f-fc9f-4488-9c26-4ffc653c0024',
+            expected: { 'library_id' => '256380', 'video_id' => 'd9d9ab1f-fc9f-4488-9c26-4ffc653c0024' } }
         ],
         'codepen' => [
           { url: 'https://codepen.io/username/pen/abcdef', expected: { 'user' => 'username', 'pen_id' => 'abcdef' } },
diff --git a/spec/enterprise/jobs/captain/inbox_pending_conversations_resolution_job_spec.rb b/spec/enterprise/jobs/captain/inbox_pending_conversations_resolution_job_spec.rb
index 63b8c1bca..f432aae62 100644
--- a/spec/enterprise/jobs/captain/inbox_pending_conversations_resolution_job_spec.rb
+++ b/spec/enterprise/jobs/captain/inbox_pending_conversations_resolution_job_spec.rb
@@ -84,6 +84,16 @@ RSpec.describe Captain::InboxPendingConversationsResolutionJob, type: :job do
       expect(resolvable_pending_conversation.reload.status).to eq('pending')
       expect(resolvable_pending_conversation.messages.outgoing).to be_empty
     end
+
+    it 'falls back to legacy time-based resolve when legacy auto-resolve is forced' do
+      inbox.account.update!(captain_auto_resolve_mode: 'legacy')
+      allow(Captain::ConversationCompletionService).to receive(:new)
+
+      described_class.perform_now(inbox)
+
+      expect(Captain::ConversationCompletionService).not_to have_received(:new)
+      expect(resolvable_pending_conversation.reload.status).to eq('resolved')
+    end
   end
 
   context 'when LLM evaluation returns complete' do
@@ -322,7 +332,7 @@ RSpec.describe Captain::InboxPendingConversationsResolutionJob, type: :job do
   end
 
   it 'does not resolve conversations when auto-resolve is disabled at execution time' do
-    inbox.account.update!(captain_disable_auto_resolve: true)
+    inbox.account.update!(captain_auto_resolve_mode: 'disabled')
 
     expect do
       described_class.perform_now(inbox)
@@ -331,4 +341,14 @@ RSpec.describe Captain::InboxPendingConversationsResolutionJob, type: :job do
     expect(resolvable_pending_conversation.reload.status).to eq('pending')
     expect(resolvable_pending_conversation.messages.outgoing).to be_empty
   end
+
+  it 'falls back to disabled mode from legacy settings key' do
+    inbox.account.update!(settings: inbox.account.settings.merge('captain_disable_auto_resolve' => true))
+
+    expect do
+      described_class.perform_now(inbox)
+    end.not_to(change { resolvable_pending_conversation.reload.status })
+
+    expect(resolvable_pending_conversation.reload.status).to eq('pending')
+  end
 end
diff --git a/spec/enterprise/jobs/enterprise/account/conversations_resolution_scheduler_job_spec.rb b/spec/enterprise/jobs/enterprise/account/conversations_resolution_scheduler_job_spec.rb
index 343100a50..1988d346c 100644
--- a/spec/enterprise/jobs/enterprise/account/conversations_resolution_scheduler_job_spec.rb
+++ b/spec/enterprise/jobs/enterprise/account/conversations_resolution_scheduler_job_spec.rb
@@ -30,12 +30,28 @@ RSpec.describe Account::ConversationsResolutionSchedulerJob, type: :job do
       end
     end
 
-    context 'when account has captain_disable_auto_resolve enabled' do
+    context 'when account has captain auto resolve disabled' do
       let!(:regular_inbox) { create(:inbox, account: account) }
 
       before do
         create(:captain_inbox, captain_assistant: assistant, inbox: regular_inbox)
-        account.update!(captain_disable_auto_resolve: true)
+        account.update!(captain_auto_resolve_mode: 'disabled')
+      end
+
+      it 'does not enqueue resolution jobs' do
+        expect do
+          described_class.perform_now
+        end.not_to have_enqueued_job(Captain::InboxPendingConversationsResolutionJob)
+          .with(regular_inbox)
+      end
+    end
+
+    context 'when account uses legacy disabled settings key' do
+      let!(:regular_inbox) { create(:inbox, account: account) }
+
+      before do
+        create(:captain_inbox, captain_assistant: assistant, inbox: regular_inbox)
+        account.update!(settings: account.settings.merge('captain_disable_auto_resolve' => true))
       end
 
       it 'does not enqueue resolution jobs' do
diff --git a/spec/enterprise/lib/captain/tools/resolve_conversation_tool_spec.rb b/spec/enterprise/lib/captain/tools/resolve_conversation_tool_spec.rb
index f676b2974..2eae2905a 100644
--- a/spec/enterprise/lib/captain/tools/resolve_conversation_tool_spec.rb
+++ b/spec/enterprise/lib/captain/tools/resolve_conversation_tool_spec.rb
@@ -41,7 +41,18 @@ RSpec.describe Captain::Tools::ResolveConversationTool do
   end
 
   describe 'when auto-resolve is disabled for the account' do
-    before { account.update!(captain_disable_auto_resolve: true) }
+    before { account.update!(captain_auto_resolve_mode: 'disabled') }
+
+    it 'does not resolve and returns a disabled message' do
+      result = tool.perform(tool_context, reason: 'Possible spam')
+
+      expect(result).to eq('Auto-resolve is disabled for this account')
+      expect(conversation.reload).not_to be_resolved
+    end
+  end
+
+  describe 'when auto-resolve is disabled via legacy settings key' do
+    before { account.update!(settings: account.settings.merge('captain_disable_auto_resolve' => true)) }
 
     it 'does not resolve and returns a disabled message' do
       result = tool.perform(tool_context, reason: 'Possible spam')
diff --git a/spec/lib/custom_markdown_renderer_spec.rb b/spec/lib/custom_markdown_renderer_spec.rb
index b329105d5..1237eae2c 100644
--- a/spec/lib/custom_markdown_renderer_spec.rb
+++ b/spec/lib/custom_markdown_renderer_spec.rb
@@ -184,12 +184,12 @@ describe CustomMarkdownRenderer do
       end
     end
 
-    context 'when link is a Bunny.net URL' do
+    context 'when link is a Bunny.net iframe URL' do
       let(:bunny_url) { 'https://iframe.mediadelivery.net/play/431789/1f105841-cad9-46fe-a70e-b7623c60797c' }
 
       it 'renders an iframe with Bunny embed code' do
         output = render_markdown_link(bunny_url)
-        expect(output).to include('src="https://iframe.mediadelivery.net/embed/431789/1f105841-cad9-46fe-a70e-b7623c60797c?autoplay=false&loop=false&muted=false&preload=true&responsive=true"')
+        expect(output).to include('src="https://player.mediadelivery.net/embed/431789/1f105841-cad9-46fe-a70e-b7623c60797c?autoplay=false&loop=false&muted=false&preload=true&responsive=true"')
         expect(output).to include('allowfullscreen')
         expect(output).to include('allow="accelerometer; gyroscope; autoplay; encrypted-media; picture-in-picture;"')
       end
@@ -200,5 +200,17 @@ describe CustomMarkdownRenderer do
         expect(output).to include('position: absolute; top: 0; height: 100%; width: 100%;')
       end
     end
+
+    context 'when link is a Bunny.net player URL' do
+      let(:bunny_url) { 'https://player.mediadelivery.net/play/431789/1f105841-cad9-46fe-a70e-b7623c60797c' }
+
+      it 'renders an iframe with Bunny embed code' do
+        output = render_markdown_link(bunny_url)
+        expect(output).to include('embed/431789/1f105841-cad9-46fe-a70e-b7623c60797c')
+        expect(output).to include('autoplay=false&loop=false&muted=false&preload=true&responsive=true')
+        expect(output).to include('allowfullscreen')
+        expect(output).to include('allow="accelerometer; gyroscope; autoplay; encrypted-media; picture-in-picture;"')
+      end
+    end
   end
 end
diff --git a/spec/models/account_spec.rb b/spec/models/account_spec.rb
index 3da958188..e010a3123 100644
--- a/spec/models/account_spec.rb
+++ b/spec/models/account_spec.rb
@@ -198,6 +198,44 @@ RSpec.describe Account do
         expect(account.settings['auto_resolve_message']).to eq(message)
       end
 
+      it 'defaults captain_auto_resolve_mode to legacy when captain_tasks is disabled' do
+        allow(account).to receive(:feature_enabled?).with('captain_tasks').and_return(false)
+
+        expect(account.captain_auto_resolve_mode).to eq('legacy')
+        expect(account).to be_captain_auto_resolve_legacy
+      end
+
+      it 'defaults captain_auto_resolve_mode to evaluated when captain_tasks is enabled' do
+        allow(account).to receive(:feature_enabled?).with('captain_tasks').and_return(true)
+
+        expect(account.captain_auto_resolve_mode).to eq('evaluated')
+        expect(account).to be_captain_auto_resolve_evaluated
+      end
+
+      it 'correctly gets and sets captain_auto_resolve_mode' do
+        account.captain_auto_resolve_mode = 'legacy'
+
+        expect(account.captain_auto_resolve_mode).to eq('legacy')
+        expect(account.settings['captain_auto_resolve_mode']).to eq('legacy')
+        expect(account).to be_captain_auto_resolve_legacy
+      end
+
+      it 'allows clearing captain_auto_resolve_mode to fall back to feature defaults' do
+        allow(account).to receive(:feature_enabled?).with('captain_tasks').and_return(false)
+        account.captain_auto_resolve_mode = nil
+
+        expect(account).to be_valid
+        expect(account.captain_auto_resolve_mode).to eq('legacy')
+        expect(account.settings['captain_auto_resolve_mode']).to be_nil
+      end
+
+      it 'falls back to disabled mode from legacy settings key' do
+        account.settings = { 'captain_disable_auto_resolve' => true }
+
+        expect(account.captain_auto_resolve_mode).to eq('disabled')
+        expect(account).to be_captain_auto_resolve_disabled
+      end
+
       it 'handles nil values correctly' do
         account.auto_resolve_after = nil
         account.auto_resolve_message = nil