diff --git a/Gemfile b/Gemfile
index da66e1473..597899b7d 100644
--- a/Gemfile
+++ b/Gemfile
@@ -27,7 +27,7 @@ gem "geared_pagination", "~> 1.2"
 gem "rqrcode"
 gem "rouge"
 gem "jbuilder"
-gem "lexxy", bc: "lexxy"
+gem "lexxy", "0.8.5.beta"
 gem "image_processing", "~> 1.14"
 gem "platform_agent"
 gem "aws-sdk-s3", require: false
diff --git a/Gemfile.lock b/Gemfile.lock
index 8db6817dc..ae84f65f6 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -1,10 +1,3 @@
-GIT
-  remote: https://github.com/basecamp/lexxy
-  revision: b7f0f1429df5fa425eac043191ae2b65edee7488
-  specs:
-    lexxy (0.7.6.beta)
-      rails (>= 8.0.2)
-
 GIT
   remote: https://github.com/basecamp/useragent
   revision: 433ca320a42db1266c4b89df74d0abdb9a880c5e
@@ -261,6 +254,8 @@ GEM
       logger (~> 1.6)
     letter_opener (1.10.0)
       launchy (>= 2.2, < 4)
+    lexxy (0.8.5.beta)
+      rails (>= 8.0.2)
     lint_roller (1.1.0)
     logger (1.7.0)
     loofah (2.25.0)
@@ -523,7 +518,7 @@ DEPENDENCIES
   jbuilder
   kamal
   letter_opener
-  lexxy!
+  lexxy (= 0.8.5.beta)
   mission_control-jobs
   mittens
   mocha
diff --git a/Gemfile.saas.lock b/Gemfile.saas.lock
index 6f9b0d088..176a5218c 100644
--- a/Gemfile.saas.lock
+++ b/Gemfile.saas.lock
@@ -21,13 +21,6 @@ GIT
       rails (>= 7.0)
       rainbow
 
-GIT
-  remote: https://github.com/basecamp/lexxy
-  revision: b7f0f1429df5fa425eac043191ae2b65edee7488
-  specs:
-    lexxy (0.7.6.beta)
-      rails (>= 8.0.2)
-
 GIT
   remote: https://github.com/basecamp/queenbee-plugin
   revision: 14312a940471e20617b38cdec7c092a01567d18b
@@ -374,6 +367,8 @@ GEM
       logger (~> 1.6)
     letter_opener (1.10.0)
       launchy (>= 2.2, < 4)
+    lexxy (0.8.5.beta)
+      rails (>= 8.0.2)
     lint_roller (1.1.0)
     logger (1.7.0)
     loofah (2.25.0)
@@ -729,7 +724,7 @@ DEPENDENCIES
   jbuilder
   kamal
   letter_opener
-  lexxy!
+  lexxy (= 0.8.5.beta)
   mission_control-jobs
   mittens
   mocha
diff --git a/app/assets/stylesheets/attachments.css b/app/assets/stylesheets/attachments.css
index 85dc7652d..8e3808ec5 100644
--- a/app/assets/stylesheets/attachments.css
+++ b/app/assets/stylesheets/attachments.css
@@ -3,8 +3,8 @@
     block-size: auto;
     display: block;
     inline-size: fit-content;
-    position: relative;
     max-inline-size: 100%;
+    position: relative;
 
     progress {
       inline-size: 100%;
@@ -35,8 +35,7 @@
 
       @supports (field-sizing: content) {
         field-sizing: content;
-        inline-size: auto;
-        min-inline-size: 20ch;
+        inline-size: 100%;
       }
     }
   }
diff --git a/app/assets/stylesheets/lexxy.css b/app/assets/stylesheets/lexxy.css
index 8fb7658ee..053f626a9 100644
--- a/app/assets/stylesheets/lexxy.css
+++ b/app/assets/stylesheets/lexxy.css
@@ -120,6 +120,10 @@
     margin-block: 1em;
   }
 
+  .lexxy-prompt-menu {
+    max-inline-size: min(35ch, calc(100% - var(--lexxy-prompt-offset-x)));
+  }
+
   /* Content
   /* ------------------------------------------------------------------------ */
 
@@ -188,4 +192,29 @@
   .attachment {
     margin-inline: 0;
   }
+
+  .attachment-gallery {
+    .attachment {
+      display: inline-block;
+      inline-size: calc(33.333% - 0.8ch);
+    }
+
+    &.attachment-gallery--2,
+    &.attachment-gallery--4 {
+      .attachment {
+        inline-size: calc(50% - 0.8ch);
+      }
+    }
+  }
+
+  action-text-attachment[content-type^='application/vnd.actiontext'] {
+    lexxy-node-delete-button {
+      inset-inline-start: -0.25ch;
+
+      .lexxy-floating-controls__group {
+        background-color: oklch(var(--lch-blue-dark));
+        border-radius: 50%;
+      }
+    }
+  }
 }
diff --git a/app/javascript/initializers/index.js b/app/javascript/initializers/index.js
index 1d16ef205..d2c20451e 100644
--- a/app/javascript/initializers/index.js
+++ b/app/javascript/initializers/index.js
@@ -1,3 +1,4 @@
 import "initializers/current"
 import "initializers/bridge/bridge_element"
 import "initializers/offline"
+import "initializers/lexxy_markdown_paste"
diff --git a/app/javascript/initializers/lexxy_markdown_paste.js b/app/javascript/initializers/lexxy_markdown_paste.js
new file mode 100644
index 000000000..cf7600306
--- /dev/null
+++ b/app/javascript/initializers/lexxy_markdown_paste.js
@@ -0,0 +1,3 @@
+document.addEventListener("lexxy:insert-markdown", (event) => {
+  event.detail.addBlockSpacing()
+})
diff --git a/test/system/smoke_test.rb b/test/system/smoke_test.rb
index 31e8f723f..5af13f890 100644
--- a/test/system/smoke_test.rb
+++ b/test/system/smoke_test.rb
@@ -76,6 +76,38 @@ class SmokeTest < ApplicationSystemTestCase
     assert_no_selector "div##{dom_id(notification)}"
   end
 
+  test "markdown paste adds block spacing" do
+    sign_in_as(users(:david))
+
+    visit card_url(cards(:layout))
+    find("lexxy-editor").click
+    paste_markdown("Hello\n\nWorld")
+
+    within("lexxy-editor") do
+      assert_selector "p", text: "Hello"
+      assert_selector "p br", visible: :all
+      assert_selector "p", text: "World"
+    end
+  end
+
+  test "markdown paste preserves line breaks" do
+    sign_in_as(users(:david))
+
+    visit card_url(cards(:layout))
+    find("lexxy-editor").click
+    paste_markdown("Hello\nWorld")
+
+    inner_html = find("lexxy-editor p", text: "Hello").native.property("innerHTML")
+    children = Nokogiri::HTML5.fragment(inner_html).children
+    assert_pattern do
+      children => [
+        { name: "span", inner_html: "Hello" },
+        { name: "br" },
+        { name: "span", inner_html: "World" }
+      ]
+    end
+  end
+
   test "dragging card to a new column" do
     sign_in_as(users(:david))
 
@@ -105,4 +137,12 @@ class SmokeTest < ApplicationSystemTestCase
       editor_element.set with
       page.execute_script("arguments[0].value = '#{with}'", editor_element)
     end
+
+    def paste_markdown(markdown)
+      page.execute_script(<<~JS, markdown)
+        const dt = new DataTransfer();
+        dt.setData("text/plain", arguments[0]);
+        document.activeElement.dispatchEvent(new ClipboardEvent("paste", { clipboardData: dt, bubbles: true }));
+      JS
+    end
 end