diff --git a/core/src/main/resources/jenkins/mvn/FilePathGlobalSettingsProvider/config.jelly b/core/src/main/resources/jenkins/mvn/FilePathGlobalSettingsProvider/config.jelly
index fcd17978b2e1..3f3ff2065305 100644
--- a/core/src/main/resources/jenkins/mvn/FilePathGlobalSettingsProvider/config.jelly
+++ b/core/src/main/resources/jenkins/mvn/FilePathGlobalSettingsProvider/config.jelly
@@ -24,7 +24,7 @@ THE SOFTWARE.
 
 <?jelly escape-by-default='true'?>
 <j:jelly xmlns:j="jelly:core" xmlns:st="jelly:stapler" xmlns:f="/lib/form">
-    <f:entry title="${%File path}" field="path">
+    <f:entry title="${%File path}" field="path" class="jenkins-!-margin-bottom-0">
         <f:textbox />
     </f:entry>
 </j:jelly>
\ No newline at end of file
diff --git a/core/src/main/resources/jenkins/mvn/GlobalMavenConfig/config.groovy b/core/src/main/resources/jenkins/mvn/GlobalMavenConfig/config.groovy
index 53a41b6b1922..7d1ff84aa72f 100644
--- a/core/src/main/resources/jenkins/mvn/GlobalMavenConfig/config.groovy
+++ b/core/src/main/resources/jenkins/mvn/GlobalMavenConfig/config.groovy
@@ -3,10 +3,6 @@ package jenkins.mvn.GlobalMavenConfig
 def f = namespace(lib.FormTagLib)
 
 f.section(title:_("Maven Configuration")) {
-    div(class: "jenkins-form-item") {
-        f.dropdownDescriptorSelector(title:_("Default settings provider"), field:"settingsProvider")
-    }
-    div(class: "jenkins-form-item") {
-        f.dropdownDescriptorSelector(title:_("Default global settings provider"), field:"globalSettingsProvider")
-    }
+  f.dropdownDescriptorSelector(title:_("Default settings provider"), field:"settingsProvider")
+  f.dropdownDescriptorSelector(title:_("Default global settings provider"), field:"globalSettingsProvider")
 }
diff --git a/core/src/main/resources/jenkins/tools/GlobalToolConfiguration/index.groovy b/core/src/main/resources/jenkins/tools/GlobalToolConfiguration/index.groovy
index 0ad0f39ffa4b..713cdba946eb 100644
--- a/core/src/main/resources/jenkins/tools/GlobalToolConfiguration/index.groovy
+++ b/core/src/main/resources/jenkins/tools/GlobalToolConfiguration/index.groovy
@@ -31,7 +31,7 @@ l.layout(permission:app.SYSTEM_READ, title:my.displayName) {
             Functions.getSortedDescriptorsForGlobalConfigByDescriptor(my.FILTER).each { Descriptor descriptor ->
                 set("descriptor",descriptor)
                 set("instance",descriptor)
-                f.rowSet(name:descriptor.jsonSafeClassName) {
+                f.rowSet(name:descriptor.jsonSafeClassName, class: "jenkins-!-margin-bottom-0") {
                     st.include(from:descriptor, page:descriptor.globalConfigPage)
                 }
             }
diff --git a/core/src/main/resources/lib/form/entry.jelly b/core/src/main/resources/lib/form/entry.jelly
index f7a9ab4d1285..8751a5ea12ec 100644
--- a/core/src/main/resources/lib/form/entry.jelly
+++ b/core/src/main/resources/lib/form/entry.jelly
@@ -52,7 +52,7 @@ THE SOFTWARE.
       This content is HTML (unless the boolean variable escapeEntryTitleAndDescription is set). Use h.escape if necessary.
     </st:attribute>
     <st:attribute name="class">
-      Classes to apply to the form
+      Classes to apply to the form item
     </st:attribute>
     <st:attribute name="help">
       URL to the HTML page. When this attribute is specified, the entry gets
@@ -96,7 +96,7 @@ THE SOFTWARE.
         </j:if>
       </j:when>
       <j:otherwise>
-        <div class="jenkins-checkbox-help-wrapper">
+        <div>
           <d:invokeBody />
           <f:helpLink url="${attrs.help}" featureName="${title}"/>
         </div>
diff --git a/core/src/main/resources/lib/form/hetero-list.jelly b/core/src/main/resources/lib/form/hetero-list.jelly
index ca50393ffaf0..7d996108740e 100644
--- a/core/src/main/resources/lib/form/hetero-list.jelly
+++ b/core/src/main/resources/lib/form/hetero-list.jelly
@@ -80,7 +80,7 @@ THE SOFTWARE.
   </st:documentation>
   <d:taglib uri="local">
     <d:tag name="body">
-      <div style="width:100%">
+      <div class="help-sibling" style="width:100%">
         <j:set var="help" value="${descriptor.helpFile}" />
 
         <div class="repeated-chunk__header">
@@ -95,14 +95,13 @@ THE SOFTWARE.
           </j:if>
         </div>
 
-        <!-- TODO: help support is unintuitive; people should be able to see help from drop-down menu -->
         <j:if test="${help!=null}">
           <f:helpArea />
         </j:if>
 
-        <d:invokeBody/>
-
         <f:class-entry descriptor="${descriptor}" />
+
+        <d:invokeBody/>
       </div>
     </d:tag>
   </d:taglib>
diff --git a/core/src/main/resources/lib/form/repeatable/repeatable.js b/core/src/main/resources/lib/form/repeatable/repeatable.js
index 3260051d1795..3d15bf122ada 100644
--- a/core/src/main/resources/lib/form/repeatable/repeatable.js
+++ b/core/src/main/resources/lib/form/repeatable/repeatable.js
@@ -173,19 +173,10 @@ Behaviour.specify("INPUT.repeatable-add", 'repeatable', 0, function(e) {
         e = null; // avoid memory leak
     });
 
-Behaviour.specify("INPUT.repeatable-delete", 'repeatable', 0, function(e) {
-        var b = makeButton(e,function(e) {
-            repeatableSupport.onDelete(e.target);
-        });
-        var be = $(b.get("element"));
-        be.on("mouseover",function() {
-            $(this).up(".repeated-chunk").addClassName("hover");
-        });
-        be.on("mouseout",function() {
-            $(this).up(".repeated-chunk").removeClassName("hover");
-        });
-
-        e = be = null; // avoid memory leak
+Behaviour.specify("BUTTON.repeatable-delete", 'repeatable', 0, function(e) {
+        e.addEventListener("click", function() {
+            repeatableSupport.onDelete(e);
+        })
     });
 
 // radio buttons in repeatable content
diff --git a/core/src/main/resources/lib/form/repeatableDeleteButton.jelly b/core/src/main/resources/lib/form/repeatableDeleteButton.jelly
index b87cf21feb8b..094a6ab82643 100644
--- a/core/src/main/resources/lib/form/repeatableDeleteButton.jelly
+++ b/core/src/main/resources/lib/form/repeatableDeleteButton.jelly
@@ -32,5 +32,7 @@ THE SOFTWARE.
     </st:attribute>
   </st:documentation>
   <st:adjunct includes="lib.form.repeatable.repeatable"/>
-  <input type="button" value="${attrs.value ?: '%Delete'}" tooltip="${attrs.value ?: '%Delete'}" class="repeatable-delete danger" />
+  <button tooltip="${attrs.value ?: '%Delete'}" class="repeatable-delete danger" type="button">
+    <l:ionicon name="close-outline" />
+  </button>
 </j:jelly>
diff --git a/core/src/main/resources/lib/form/rowSet.jelly b/core/src/main/resources/lib/form/rowSet.jelly
index 94468d70a689..2ede2c842d40 100644
--- a/core/src/main/resources/lib/form/rowSet.jelly
+++ b/core/src/main/resources/lib/form/rowSet.jelly
@@ -38,6 +38,9 @@ THE SOFTWARE.
     <st:attribute name="isFormItem">
       Removes the "jenkins-form-item" class if false
     </st:attribute>
+    <st:attribute name="class">
+      Classes to apply to the container (this will be the form item if 'isFormItem' is true)
+    </st:attribute>
   </st:documentation>
 
   <j:choose>
@@ -46,7 +49,7 @@ THE SOFTWARE.
       <d:invokeBody />
     </j:when>
     <j:otherwise>
-      <div class="${isFormItem.equals('false') ? '' : 'jenkins-form-item'}">
+      <div class="${isFormItem.equals('false') ? '' : 'jenkins-form-item'} ${class}">
         <div ref="${attrs.ref}" class="row-set-start row-group-start tr" style="display:none" name="${attrs.name}"></div>
         <d:invokeBody />
         <div class="row-set-end row-group-end tr"></div>
diff --git a/war/src/main/js/widgets/config/tabbar.less b/war/src/main/js/widgets/config/tabbar.less
index 50060bf72db2..1d3170f10f2d 100644
--- a/war/src/main/js/widgets/config/tabbar.less
+++ b/war/src/main/js/widgets/config/tabbar.less
@@ -158,78 +158,6 @@
         }
       }
 
-      // Repeatable elements
-
-      .repeated-container > .repeated-chunk {
-        padding: 0.75rem;
-      }
-
-      .repeated-chunk.hover {
-        border-color: var(--line-blue);
-        box-shadow: 0 2px 10px var(--shade), inset 0 200px 200px -200px var(--brightest-bg-color);
-        position: relative;
-        z-index: 2
-      }
-
-      .repeated-chunk {
-        border: 1px solid var(--shade);
-        margin: 2px;
-        position: relative;
-      }
-      // Styling for drag & drop items
-      .repeated-chunk.repeated-chunk--sortable-ghost,
-      .repeated-chunk.repeated-chunk--sortable-chosen {
-        border-width: 2px;
-        border-color: var(--line-blue);
-      }
-
-      .repeatable-delete {
-        position: absolute;
-        top: -4px;
-        right: 40px;
-        height: 20px;
-        width: 30px;
-      }
-
-      .repeatable-delete button {
-        text-align: center;
-        text-indent: -9999px;
-        width: 30px !important;
-        height: 18px !important;
-        padding: 0 !important;
-        margin: 0 !important;
-        .border-radius-top(0) !important;
-        background-color: var(--danger);
-        color: var(--light-bg-color);
-        border: 1px solid var(--danger-line);
-        line-height: 12px !important;
-        display: inline-block;
-        font-size: 8px;
-        min-width: 0;
-        min-height: 0;
-
-        &:focus,
-        &:hover {
-          background-color: var(--danger-dark);
-          border-color: var(--danger-dark-line);
-          color: var(--brightest-bg-color);
-        }
-
-        &:before {
-          content: 'X';
-          font-weight: bold;
-          position: absolute;
-          display: block;
-          left: 0;
-          top: 2;
-          width: 30px;
-          height: 16px;
-          text-align: center;
-          font-size: 12px;
-          text-indent: 0;
-        }
-      }
-
       span.highlight {
         background-color: #ffff00;
       }
diff --git a/war/src/main/less/base/style.less b/war/src/main/less/base/style.less
index 33fce73e72bc..0043ec30c397 100644
--- a/war/src/main/less/base/style.less
+++ b/war/src/main/less/base/style.less
@@ -924,15 +924,16 @@ table.parameters > tbody:hover {
 
 /* ========================= editable combobox style ========================= */
 .comboBoxList {
-  border: 1px solid #000;
   overflow: visible;
-  background-color: white;
-  color: black;
+  background-color: var(--background);
+  color: var(--text-color);
+  border-radius: var(--form-input-border-radius);
+  box-shadow: 0 10px 20px rgba(black, 0.1);
 }
 
 .comboBoxSelectedItem {
-  background-color: Highlight;
-  color: HighlightText;
+  background-color: var(--primary);
+  color: var(--text-color);
 }
 
 .combobox-values {
@@ -1112,54 +1113,6 @@ table.fingerprint-in-build td {
     border-radius: 0.25em;
 }
 
-/* ========================= repeatable elements ========================= */
-
-.repeated-chunk {
-    border: 2px dashed var(--input-border);
-    padding: 1rem;
-  border-radius: 6px;
-}
-
-.repeated-chunk.hover {
-    border-color: var(--medium-grey);
-}
-
-.repeated-chunk .show-if-last { visibility: hidden; }
-.repeated-chunk.last .show-if-last { visibility: visible; }
-
-.repeated-chunk .show-if-not-last { visibility: visible; }
-.repeated-chunk.last .show-if-not-last { visibility: hidden; }
-
-.repeated-chunk .show-if-not-only { visibility: visible; }
-.repeated-chunk.only .show-if-not-only { visibility: hidden; }
-
-/* == nested repeatable elements / 2 deep == */
-.repeated-chunk .repeated-chunk .show-if-last { visibility: hidden; }
-.repeated-chunk .repeated-chunk.last .show-if-last { visibility: visible; }
-
-.repeated-chunk .repeated-chunk .show-if-not-last { visibility: visible; }
-.repeated-chunk .repeated-chunk.last .show-if-not-last { visibility: hidden; }
-
-.repeated-chunk .repeated-chunk .show-if-not-only { visibility: visible; }
-.repeated-chunk .repeated-chunk.only .show-if-not-only { visibility: hidden; }
-
-/* == nested repeatable elements / 3 deep == */
-.repeated-chunk .repeated-chunk .repeated-chunk .show-if-last { visibility: hidden; }
-.repeated-chunk .repeated-chunk .repeated-chunk.last .show-if-last { visibility: visible; }
-
-.repeated-chunk .repeated-chunk .repeated-chunk .show-if-not-last { visibility: visible; }
-.repeated-chunk .repeated-chunk .repeated-chunk.last .show-if-not-last { visibility: hidden; }
-
-.repeated-chunk .repeated-chunk .repeated-chunk .show-if-not-only { visibility: visible; }
-.repeated-chunk .repeated-chunk .repeated-chunk.only .show-if-not-only { visibility: hidden; }
-
-/*
-    <DIV>s marked with to-be-removed is used in conjunction with repeatable.jelly and hetero-list.jelly
-    and represents a master copy that gets pulled out from HTML, then inserted later upon demand multiple times
-    when the user does "Add".
-*/
-div.to-be-removed { display: none; }
-
 /* ========================= Other form related CSS ========================= */
 
 .radioBlock-container {
@@ -1201,6 +1154,7 @@ div.to-be-removed { display: none; }
   opacity: 0!important;
   max-height: 0!important;
   height: 0!important;
+  overflow: hidden;
 }
 
 .row-set-end { display: none; }
@@ -1231,31 +1185,6 @@ textarea.rich-editor {
   visibility: hidden;
 }
 
-/* ========================= D&D support in heterogenous/repeatable lists = */
-
-.hetero-list-container.with-drag-drop .repeated-chunk,
-.repeated-container.with-drag-drop .repeated-chunk {
-    margin-top: 0.5em;
-    margin-bottom: 0.5em;
-}
-
-// SortableJS drag & drop classes
-.repeated-chunk--sortable-ghost {
-  height: 100px;
-  width: 100%;
-  overflow: hidden;
-}
-.repeated-chunk--sortable-chosen {
-  height: 100px;
-  width: 100%;
-  background-color: transparent;
-  border: 2px solid var(--primary);
-
-  & > * {
-    display: none;
-  }
-}
-
 /* ========================= plugin update center ========================= */
 
 #plugins .excerpt {
diff --git a/war/src/main/less/base/yui-compatibility.less b/war/src/main/less/base/yui-compatibility.less
index 655054472655..a7df1a601559 100644
--- a/war/src/main/less/base/yui-compatibility.less
+++ b/war/src/main/less/base/yui-compatibility.less
@@ -216,3 +216,8 @@ div.yahooTree td {
     display: inline-block;
   }
 }
+
+.yui-panel,
+.yui-panel .bd {
+  background-color: var(--background) !important;
+}
\ No newline at end of file
diff --git a/war/src/main/less/modules/draggable-card.less b/war/src/main/less/modules/draggable-card.less
index 272c7f3164ad..10246b3e3273 100644
--- a/war/src/main/less/modules/draggable-card.less
+++ b/war/src/main/less/modules/draggable-card.less
@@ -1,43 +1,195 @@
+/* ========================= repeatable elements ========================= */
+
+.repeated-chunk {
+  position: relative;
+  border: 2px dashed var(--input-border);
+  padding: 1rem;
+  border-radius: 10px;
+}
+
+.repeated-chunk .show-if-last { visibility: hidden; }
+.repeated-chunk.last .show-if-last { visibility: visible; }
+
+.repeated-chunk .show-if-not-last { visibility: visible; }
+.repeated-chunk.last .show-if-not-last { visibility: hidden; }
+
+.repeated-chunk .show-if-not-only { visibility: visible; }
+.repeated-chunk.only .show-if-not-only { visibility: hidden; }
+
+/* == nested repeatable elements / 2 deep == */
+.repeated-chunk .repeated-chunk .show-if-last { visibility: hidden; }
+.repeated-chunk .repeated-chunk.last .show-if-last { visibility: visible; }
+
+.repeated-chunk .repeated-chunk .show-if-not-last { visibility: visible; }
+.repeated-chunk .repeated-chunk.last .show-if-not-last { visibility: hidden; }
+
+.repeated-chunk .repeated-chunk .show-if-not-only { visibility: visible; }
+.repeated-chunk .repeated-chunk.only .show-if-not-only { visibility: hidden; }
+
+/* == nested repeatable elements / 3 deep == */
+.repeated-chunk .repeated-chunk .repeated-chunk .show-if-last { visibility: hidden; }
+.repeated-chunk .repeated-chunk .repeated-chunk.last .show-if-last { visibility: visible; }
+
+.repeated-chunk .repeated-chunk .repeated-chunk .show-if-not-last { visibility: visible; }
+.repeated-chunk .repeated-chunk .repeated-chunk.last .show-if-not-last { visibility: hidden; }
+
+.repeated-chunk .repeated-chunk .repeated-chunk .show-if-not-only { visibility: visible; }
+.repeated-chunk .repeated-chunk .repeated-chunk.only .show-if-not-only { visibility: hidden; }
+
+/*
+    <DIV>s marked with to-be-removed is used in conjunction with repeatable.jelly and hetero-list.jelly
+    and represents a master copy that gets pulled out from HTML, then inserted later upon demand multiple times
+    when the user does "Add".
+*/
+div.to-be-removed { display: none; }
+
+/* ========================= D&D support in heterogenous/repeatable lists = */
+
+.hetero-list-container.with-drag-drop .repeated-chunk,
+.repeated-container.with-drag-drop .repeated-chunk {
+  margin-bottom: 1rem;
+}
+
+// SortableJS drag & drop classes
+.repeated-chunk--sortable-ghost {
+  height: 100px;
+  width: 100%;
+  overflow: hidden;
+}
+
+.repeated-chunk--sortable-chosen {
+  width: 100%;
+  height: 100px;
+  background-color: transparent;
+  border: 2px solid var(--primary);
+
+  & > * {
+    display: none;
+  }
+}
+
 .repeated-chunk {
+  & > div > *:last-of-type {
+    margin-bottom: 0;
+  }
+
   &__header {
     display: flex;
     align-items: center;
     justify-content: flex-start;
     font-weight: bold;
+    margin-top: -0.4rem;
     margin-bottom: 0.75rem;
 
     .dd-handle {
       position: relative;
-      width: 22px;
-      height: 22px;
+      width: 30px;
+      height: 30px;
       overflow: hidden;
       margin-right: 0.75rem;
       cursor: move;
+      margin-left: -6px;
+
+      &::before {
+        content: "";
+        position: absolute;
+        top: 0;
+        left: 0;
+        bottom: 0;
+        right: 0;
+        background: var(--text-color);
+        border-radius: var(--form-input-border-radius);
+        opacity: 0;
+        transition: var(--standard-transition);
+      }
 
       &::after {
         content: "";
         position: absolute;
-        top: 1px;
+        top: 0;
         left: 4px;
+        bottom: 0;
         right: 4px;
-        height: 20px;
-        background-image: url("data:image/svg+xml,%3C%3Fxml version='1.0' encoding='UTF-8'%3F%3E%3Csvg width='9px' height='19px' viewBox='0 0 9 19' version='1.1' xmlns='http://www.w3.org/2000/svg' xmlns:xlink='http://www.w3.org/1999/xlink'%3E%3Ctitle%3EShape%3C/title%3E%3Cg id='Page-1' stroke='none' stroke-width='1' fill='none' fill-rule='evenodd'%3E%3Cpath d='M2,15 C3.10456949,15 4,15.8954305 4,17 C4,18.1045695 3.10456949,19 2,19 C0.89543051,19 0,18.1045695 0,17 C0,15.8954305 0.89543051,15 2,15 Z M7,15 C8.10456949,15 9,15.8954305 9,17 C9,18.1045695 8.10456949,19 7,19 C5.89543051,19 5,18.1045695 5,17 C5,15.8954305 5.89543051,15 7,15 Z M2,16 C1.44771525,16 1,16.4477153 1,17 C1,17.5128358 1.38604019,17.9355072 1.88337887,17.9932723 L2,18 L2.11662113,17.9932723 C2.61395981,17.9355072 3,17.5128358 3,17 C3,16.4477153 2.55228475,16 2,16 Z M7,16 C6.44771525,16 6,16.4477153 6,17 C6,17.5128358 6.38604019,17.9355072 6.88337887,17.9932723 L7,18 L7.11662113,17.9932723 C7.61395981,17.9355072 8,17.5128358 8,17 C8,16.4477153 7.55228475,16 7,16 Z M2,10 C3.1045695,10 4,10.8954305 4,12 C4,13.1045695 3.1045695,14 2,14 C0.8954305,14 0,13.1045695 0,12 C0,10.8954305 0.8954305,10 2,10 Z M7,10 C8.1045695,10 9,10.8954305 9,12 C9,13.1045695 8.1045695,14 7,14 C5.8954305,14 5,13.1045695 5,12 C5,10.8954305 5.8954305,10 7,10 Z M2,11 C1.44771525,11 1,11.4477152 1,12 C1,12.5128358 1.38604019,12.9355072 1.88337887,12.9932723 L2,13 L2.11662113,12.9932723 C2.61395981,12.9355072 3,12.5128358 3,12 C3,11.4477152 2.55228475,11 2,11 Z M7,11 C6.44771525,11 6,11.4477152 6,12 C6,12.5128358 6.38604019,12.9355072 6.88337887,12.9932723 L7,13 L7.11662113,12.9932723 C7.61395981,12.9355072 8,12.5128358 8,12 C8,11.4477152 7.55228475,11 7,11 Z M2,5 C3.1045695,5 4,5.8954305 4,7 C4,8.1045695 3.1045695,9 2,9 C0.8954305,9 0,8.1045695 0,7 C0,5.8954305 0.8954305,5 2,5 Z M7,5 C8.1045695,5 9,5.8954305 9,7 C9,8.1045695 8.1045695,9 7,9 C5.8954305,9 5,8.1045695 5,7 C5,5.8954305 5.8954305,5 7,5 Z M2,6 C1.44771525,6 1,6.44771525 1,7 C1,7.51283584 1.38604019,7.93550716 1.88337887,7.99327227 L2,8 L2.11662113,7.99327227 C2.61395981,7.93550716 3,7.51283584 3,7 C3,6.44771525 2.55228475,6 2,6 Z M7,6 C6.44771525,6 6,6.44771525 6,7 C6,7.51283584 6.38604019,7.93550716 6.88337887,7.99327227 L7,8 L7.11662113,7.99327227 C7.61395981,7.93550716 8,7.51283584 8,7 C8,6.44771525 7.55228475,6 7,6 Z M2,0 C3.1045695,0 4,0.8954305 4,2 C4,3.1045695 3.1045695,4 2,4 C0.8954305,4 0,3.1045695 0,2 C0,0.8954305 0.8954305,0 2,0 Z M7,0 C8.1045695,0 9,0.8954305 9,2 C9,3.1045695 8.1045695,4 7,4 C5.8954305,4 5,3.1045695 5,2 C5,0.8954305 5.8954305,0 7,0 Z M2,1 C1.44771525,1 1,1.44771525 1,2 C1,2.51283584 1.38604019,2.93550716 1.88337887,2.99327227 L2,3 L2.11662113,2.99327227 C2.61395981,2.93550716 3,2.51283584 3,2 C3,1.44771525 2.55228475,1 2,1 Z M7,1 C6.44771525,1 6,1.44771525 6,2 C6,2.51283584 6.38604019,2.93550716 6.88337887,2.99327227 L7,3 L7.11662113,2.99327227 C7.61395981,2.93550716 8,2.51283584 8,2 C8,1.44771525 7.55228475,1 7,1 Z' id='Shape' fill='%23FFFFFF' fill-rule='nonzero'%3E%3C/path%3E%3C/g%3E%3C/svg%3E");
-        background-repeat: no-repeat;
-        background-position: left top;
+        background-color: var(--text-color);
+        mask-image: url("data:image/svg+xml,%3Csvg xmlns='http://www.w3.org/2000/svg' class='ionicon' viewBox='0 0 512 512'%3E%3Ctitle%3EReorder Three%3C/title%3E%3Cpath fill='none' stroke='currentColor' stroke-linecap='round' stroke-linejoin='round' stroke-width='32' d='M96 256h320M96 176h320M96 336h320'/%3E%3C/svg%3E");
+        mask-position: center;
+        mask-repeat: no-repeat;
+        mask-size: contain;
       }
 
       &:hover {
-        &::after {
-          opacity: 0.75;
+        &::before {
+          opacity: 0.1;
         }
       }
     }
+  }
+
+  // TODO: Update/remove when .jenkins-button PR is merged
+  .repeatable-delete {
+    position: absolute;
+    top: 0.6rem;
+    right: 0.6rem;
+    display: flex;
+    align-items: center;
+    justify-content: center;
+    width: 28px;
+    height: 28px;
+    border: none;
+    outline: none;
+    margin-left: auto;
+    color: var(--red);
+    z-index: 0;
+    background: transparent;
+    cursor: pointer;
+
+    &::before {
+      content: "";
+      position: absolute;
+      top: 0;
+      left: 0;
+      bottom: 0;
+      right: 0;
+      background: currentColor;
+      border-radius: 100px;
+      z-index: -1;
+      opacity: 0.075;
+      transition: var(--standard-transition);
+    }
+
+    &::after {
+      content: "";
+      position: absolute;
+      top: 0;
+      left: 0;
+      bottom: 0;
+      right: 0;
+      box-shadow: 0 0 0 10px transparent;
+      border-radius: 100px;
+      z-index: -1;
+      opacity: 0.075;
+      transition: var(--standard-transition);
+    }
+
+    svg {
+      width: 18px;
+      height: 18px;
+    }
+
+    &:hover {
+      &::before {
+        opacity: 0.1;
+      }
+    }
 
-    .yui-button {
-      margin-left: auto;
+    &:active,
+    &:focus {
+      &::before {
+        opacity: 0.15;
+      }
 
-      * {
-        margin: 0;
+      &::after {
+        box-shadow: 0 0 0 5px var(--red);
       }
     }
   }
diff --git a/war/src/main/less/modules/form.less b/war/src/main/less/modules/form.less
index 0ff5d62b5987..1c7555496aa8 100644
--- a/war/src/main/less/modules/form.less
+++ b/war/src/main/less/modules/form.less
@@ -227,14 +227,15 @@
   &::after {
     content: "";
     position: absolute;
-    top: 13px;
-    right: 15px;
-    width: 8px;
-    height: 8px;
-    color: inherit;
-    border-bottom: 2px solid currentColor;
-    border-right: 2px solid currentColor;
-    transform: rotate(45deg);
+    top: 0;
+    right: 13px;
+    bottom: 0;
+    width: 12px;
+    background-color: currentColor;
+    mask-image: url("data:image/svg+xml;charset=UTF-8,%3c?xml version='1.0' encoding='UTF-8'?%3e%3csvg width='336px' height='192px' viewBox='0 0 336 192' version='1.1' xmlns='http://www.w3.org/2000/svg' xmlns:xlink='http://www.w3.org/1999/xlink'%3e%3ctitle%3ePath%3c/title%3e%3cg id='Page-1' stroke='none' stroke-width='1' fill='none' fill-rule='evenodd'%3e%3cg id='arrow' transform='translate(0.000000, 0.000000)' fill='%23FF0000' fill-rule='nonzero'%3e%3cpath d='M7.02943725,7.02943725 C16.3053957,-2.24652118 31.2852799,-2.34214962 40.6788451,6.74255194 L40.9705627,7.02943725 L168,134.059 L295.029437,7.02943725 C304.305396,-2.24652118 319.28528,-2.34214962 328.678845,6.74255194 L328.970563,7.02943725 C338.246521,16.3053957 338.34215,31.2852799 329.257448,40.6788451 L328.970563,40.9705627 L184.970563,184.970563 C175.694604,194.246521 160.71472,194.34215 151.321155,185.257448 L151.029437,184.970563 L7.02943725,40.9705627 C-2.34314575,31.5979797 -2.34314575,16.4020203 7.02943725,7.02943725 Z' id='Path'%3e%3c/path%3e%3c/g%3e%3c/g%3e%3c/svg%3e");
+    mask-size: contain;
+    mask-repeat: no-repeat;
+    mask-position: center;
     pointer-events: none;
   }
 
@@ -372,12 +373,18 @@
   }
 }
 
+// Align help buttons correctly with checkboxes
+
 .jenkins-checkbox-help-wrapper {
   display: flex;
   align-items: center;
   justify-content: flex-start;
 }
 
+.jenkins-checkbox + a.jenkins-help-button {
+  vertical-align: top;
+}
+
 .jenkins-checkbox {
   position: relative;
   display: inline-flex;
@@ -437,7 +444,7 @@
   }
 
   &::after {
-    content: "✓";
+    content: "";
     display: flex;
     align-items: center;
     justify-content: center;
@@ -447,11 +454,13 @@
     right: 0;
     width: 22px;
     height: 22px;
-    font-weight: 800;
-    color: var(--background);
-    transition: 0.2s ease;
+    background: var(--background);
+    mask-image: url("data:image/svg+xml;charset=UTF-8,%3c?xml version='1.0' encoding='UTF-8'?%3e%3csvg width='384px' height='320px' viewBox='0 0 384 320' version='1.1' xmlns='http://www.w3.org/2000/svg' xmlns:xlink='http://www.w3.org/1999/xlink'%3e%3ctitle%3ePath%3c/title%3e%3cg id='Page-1' stroke='none' stroke-width='1' fill='none' fill-rule='evenodd'%3e%3cpath d='M327.917546,10.9278525 C339.555371,-2.37251966 359.771775,-3.72027991 373.072147,7.91754577 C386.239516,19.4389932 387.692129,39.368305 376.427694,52.671077 L376.082454,53.0721475 L152.082454,309.072147 C140.014868,322.863675 118.889432,323.700972 105.767743,311.015951 L105.372583,310.627417 L9.372583,214.627417 C-3.12419433,202.13064 -3.12419433,181.86936 9.372583,169.372583 C21.7443926,157.000773 41.7261905,156.877055 54.2501999,169.001429 L54.627417,169.372583 L126.441,241.186 L327.917546,10.9278525 Z' id='Path' fill='%23FF0000' fill-rule='nonzero'%3e%3c/path%3e%3c/g%3e%3c/svg%3e");
+    mask-size: 10px 10px;
+    mask-repeat: no-repeat;
+    mask-position: center;
+    transition: var(--standard-transition);
     transform: scale(0);
-    font-size: 12px;
   }
 
   &:hover {
@@ -462,6 +471,7 @@
 
   &:active, &:focus {
     &::before {
+      border: 5px solid var(--focus-input-border);
       box-shadow: 0 0 0 5px var(--focus-input-glow);
     }
   }
@@ -627,3 +637,8 @@
     }
   }
 }
+
+// TODO Remove when https://github.com/jenkinsci/jenkins/pull/5916 is merged in
+.jenkins-\!-margin-bottom-0 {
+  margin-bottom: 0 !important;
+}
diff --git a/war/src/main/less/modules/tooltips.less b/war/src/main/less/modules/tooltips.less
index 8c1b499c1985..395d9b44b532 100644
--- a/war/src/main/less/modules/tooltips.less
+++ b/war/src/main/less/modules/tooltips.less
@@ -8,4 +8,5 @@
   font-size: 0.8rem;
   z-index: 40;
   overflow: hidden;
+  max-width: none !important;
 }
diff --git a/war/src/main/resources/images/ionicons/close-outline.svg b/war/src/main/resources/images/ionicons/close-outline.svg
new file mode 100644
index 000000000000..7ff315739e50
--- /dev/null
+++ b/war/src/main/resources/images/ionicons/close-outline.svg
@@ -0,0 +1 @@
+<svg xmlns="http://www.w3.org/2000/svg" class="ionicon" viewBox="0 0 512 512"><title>Close</title><path fill="none" stroke="currentColor" stroke-linecap="round" stroke-linejoin="round" stroke-width="32" d="M368 368L144 144M368 144L144 368"/></svg>
\ No newline at end of file
diff --git a/war/src/main/webapp/scripts/hudson-behavior.js b/war/src/main/webapp/scripts/hudson-behavior.js
index 2174329378b0..5834b24b8b08 100644
--- a/war/src/main/webapp/scripts/hudson-behavior.js
+++ b/war/src/main/webapp/scripts/hudson-behavior.js
@@ -2349,7 +2349,7 @@ var hoverNotification = (function() {
 // Decrease vertical padding for checkboxes
 window.addEventListener('load', function () {
     document.querySelectorAll(".jenkins-form-item").forEach(function (element) {
-        if (element.querySelector("input[type='checkbox']") != null && element.querySelector(".advancedLink") == null) {
+        if (element.querySelector(":scope > .optionalBlock-container > .row-group-start input[type='checkbox'], :scope > .optional-block-start input[type='checkbox'], :scope > div > .jenkins-checkbox") != null) {
             element.classList.add("jenkins-form-item--tight")
         }
     });