diff --git a/core/src/main/resources/hudson/tools/InstallSourceProperty/config.jelly b/core/src/main/resources/hudson/tools/InstallSourceProperty/config.jelly
index d9d8012101e1..f9f0b8275825 100644
--- a/core/src/main/resources/hudson/tools/InstallSourceProperty/config.jelly
+++ b/core/src/main/resources/hudson/tools/InstallSourceProperty/config.jelly
@@ -28,7 +28,7 @@ THE SOFTWARE.
           <j:arg value="${toolDescriptor.clazz}" type="java.lang.Class" />
         </j:invokeStatic>
         <f:hetero-list name="installers" items="${instance.installers}" descriptors="${descriptors}"
-                       addCaption="${%Add Installer}" deleteCaption="${%Delete Installer}"
+                       addCaption="${%Add Installer}"
                        hasHeader="true"/>
     </f:block>
 </j:jelly>
diff --git a/core/src/main/resources/hudson/tools/ToolInstallation/global.jelly b/core/src/main/resources/hudson/tools/ToolInstallation/global.jelly
index 317b0dd48151..d903402f34a4 100644
--- a/core/src/main/resources/hudson/tools/ToolInstallation/global.jelly
+++ b/core/src/main/resources/hudson/tools/ToolInstallation/global.jelly
@@ -38,7 +38,7 @@ THE SOFTWARE.
               <st:include page="config.jelly" from="${descriptor}" class="${descriptor.clazz}"/>
               <f:descriptorList descriptors="${descriptor.propertyDescriptors}" field="properties"/>
               <l:isAdmin>
-                <f:repeatableDeleteButton value="${%label.delete(descriptor.displayName)}"/>
+                <f:repeatableDeleteButton />
               </l:isAdmin>
             </div>
           </f:repeatable>
diff --git a/core/src/main/resources/lib/form/hetero-list.jelly b/core/src/main/resources/lib/form/hetero-list.jelly
index b817c936c4e8..e20d9a85c47f 100644
--- a/core/src/main/resources/lib/form/hetero-list.jelly
+++ b/core/src/main/resources/lib/form/hetero-list.jelly
@@ -81,27 +81,30 @@ THE SOFTWARE.
   </st:documentation>
   <d:taglib uri="local">
     <d:tag name="body">
-      <div class="help-sibling" style="width:100%">
-        <j:set var="help" value="${descriptor.helpFile}" />
+      <j:set var="help" value="${descriptor.helpFile}" />
+      <j:set var="disableHandle" value="${attrs.disableDragAndDrop or readOnlyMode}" />
 
-        <div class="repeated-chunk__header">
-          <div class="${attrs.disableDragAndDrop or readOnlyMode ? '' : 'dd-handle'}"/>
+      <div class="repeated-chunk__header ${disableHandle ? 'repeated-chunk__header--no-handle' : ''}">
+        <j:if test="${!disableHandle}">
+          <div class="dd-handle" />
+        </j:if>
 
-          ${descriptor.displayName}
+        ${descriptor.displayName}
 
-          <f:helpLink url="${help}"/>
+        <f:helpLink url="${help}"/>
 
-          <j:if test="${!readOnlyMode}">
-            <f:repeatableDeleteButton value="${attrs.deleteCaption}" />
-          </j:if>
-        </div>
+        <j:if test="${!readOnlyMode}">
+          <f:repeatableDeleteButton value="${attrs.deleteCaption}" />
+        </j:if>
+      </div>
 
+      <f:class-entry descriptor="${descriptor}" />
+
+      <div class="jenkins-repeated-chunk__content">
         <j:if test="${help!=null}">
           <f:helpArea />
         </j:if>
 
-        <f:class-entry descriptor="${descriptor}" />
-
         <d:invokeBody/>
       </div>
     </d:tag>
@@ -120,7 +123,7 @@ THE SOFTWARE.
       </div>
     </j:forEach>
 
-    <div class="repeatable-insertion-point" />
+    <template class="repeatable-insertion-point" />
 
     <div class="prototypes to-be-removed">
       <!-- render one prototype for each type -->
@@ -153,10 +156,8 @@ THE SOFTWARE.
     </div>
 
     <j:if test="${!readOnlyMode}">
-      <div>
-        <button type="button" class="jenkins-button hetero-list-add" menualign="${attrs.menuAlign}" suffix="${attrs.name}">${attrs.addCaption?:'%Add'}<l:icon src="symbol-chevron-down"/>
-        </button>
-      </div>
+      <button type="button" class="jenkins-button hetero-list-add" menualign="${attrs.menuAlign}" suffix="${attrs.name}">${attrs.addCaption?:'%Add'}<l:icon src="symbol-chevron-down"/>
+      </button>
     </j:if>
   </div>
 </j:jelly>
diff --git a/core/src/main/resources/lib/form/repeatable.jelly b/core/src/main/resources/lib/form/repeatable.jelly
index 8df3d44a4c61..d2ef5c80d658 100644
--- a/core/src/main/resources/lib/form/repeatable.jelly
+++ b/core/src/main/resources/lib/form/repeatable.jelly
@@ -136,10 +136,12 @@ THE SOFTWARE.
       <div class="repeated-chunk__header">
         <j:if test="${!empty(header)}"><div class="${readOnlyMode ? '' : 'dd-handle'}"/>${header}</j:if>
       </div>
-      <j:scope>
-        <j:set var="${var}" value="${null}"/>
-        <d:invokeBody />
-      </j:scope>
+      <div class="jenkins-repeated-chunk__content">
+        <j:scope>
+          <j:set var="${var}" value="${null}"/>
+          <d:invokeBody />
+        </j:scope>
+      </div>
     </div>
     <j:if test="${!empty(items) and !attrs.noAddButton and attrs.enableTopButton}">
       <button type="button" class="jenkins-button repeatable-add repeatable-add-top">
@@ -153,7 +155,9 @@ THE SOFTWARE.
         <div class="repeated-chunk__header">
           <j:if test="${!empty(header)}"><div class="${readOnlyMode ? '' : 'dd-handle'}"/>${header}</j:if>
         </div>
-        <d:invokeBody />
+        <div class="jenkins-repeated-chunk__content">
+          <d:invokeBody />
+        </div>
       </div>
     </j:forEach>
     <j:remove var="${var}" />
@@ -165,12 +169,14 @@ THE SOFTWARE.
           <div class="repeated-chunk__header">
             <j:if test="${!empty(header)}"><div class="${readOnlyMode ? '' : 'dd-handle'}"/>${header}</j:if>
           </div>
-          <d:invokeBody />
+          <div class="jenkins-repeated-chunk__content">
+            <d:invokeBody />
+          </div>
         </div>
       </j:forEach>
     </j:if>
 
-    <div class="repeatable-insertion-point" />
+    <template class="repeatable-insertion-point" />
     <j:if test="${!attrs.noAddButton}">
       <button type="button" class="jenkins-button repeatable-add">
         ${attrs.add?:'%Add'}
diff --git a/core/src/main/resources/lib/form/repeatable/repeatable.js b/core/src/main/resources/lib/form/repeatable/repeatable.js
index 3f19dcfb7e7f..6f3b9dc6ac04 100644
--- a/core/src/main/resources/lib/form/repeatable/repeatable.js
+++ b/core/src/main/resources/lib/form/repeatable/repeatable.js
@@ -40,8 +40,6 @@ var repeatableSupport = {
       addOnTop = false;
     }
 
-    // importNode isn't supported in IE.
-    // nc = document.importNode(node,true);
     var nc = document.createElement("div");
     nc.className = "repeated-chunk fade-in";
     nc.setAttribute("name", this.name);
@@ -59,7 +57,6 @@ var repeatableSupport = {
       registerSortableDragDrop(nc);
     }
 
-    nc.classList.remove("fade-in");
     Behaviour.applySubtree(nc, true);
     this.update();
   },
@@ -101,13 +98,13 @@ var repeatableSupport = {
           parentOfButton.insertBefore(addTopButton, parentOfButton.firstChild);
           Behaviour.applySubtree(addTopButton, true);
         }
-        children[0].className = "repeated-chunk first last only";
+        children[0].className = "repeated-chunk fade-in first last only";
       } else {
-        children[0].className = "repeated-chunk first";
+        children[0].className = "repeated-chunk first fade-in";
         for (var i = 1; i < children.length - 1; i++) {
-          children[i].className = "repeated-chunk middle";
+          children[i].className = "repeated-chunk middle fade-in";
         }
-        children[children.length - 1].className = "repeated-chunk last";
+        children[children.length - 1].className = "repeated-chunk last fade-in";
       }
     }
   },
@@ -133,6 +130,7 @@ var repeatableSupport = {
       // transition end not triggered in tests
       n.ontransitionend.call(n, {});
     }
+
     n.style.maxHeight = n.offsetHeight + "px";
     n.classList.add("fade-out");
     setTimeout(() => {
diff --git a/core/src/main/resources/lib/form/repeatableDeleteButton.jelly b/core/src/main/resources/lib/form/repeatableDeleteButton.jelly
index 2a1a97df4b22..41ccdf28026b 100644
--- a/core/src/main/resources/lib/form/repeatableDeleteButton.jelly
+++ b/core/src/main/resources/lib/form/repeatableDeleteButton.jelly
@@ -32,7 +32,10 @@ THE SOFTWARE.
     </st:attribute>
   </st:documentation>
   <st:adjunct includes="lib.form.repeatable.repeatable"/>
-  <button tooltip="${attrs.value ?: '%Delete'}" class="repeatable-delete danger" type="button">
+
+  <j:set var="deleteText" value="${attrs.value ?: '%Delete'}" />
+  <button class="repeatable-delete danger" type="button" style="--width: calc(${deleteText.length()}ch + 20px)">
     <l:icon src="symbol-close" />
+    <span>${deleteText}</span>
   </button>
 </j:jelly>
diff --git a/core/src/main/resources/lib/form/repeatableProperty.jelly b/core/src/main/resources/lib/form/repeatableProperty.jelly
index e94c0b4c983d..7f913deb2caa 100644
--- a/core/src/main/resources/lib/form/repeatableProperty.jelly
+++ b/core/src/main/resources/lib/form/repeatableProperty.jelly
@@ -77,9 +77,7 @@ THE SOFTWARE.
 
 
   <f:repeatable field="${attrs.field}" default="${attrs.default}" noAddButton="${attrs.noAddButton}" header="${attrs.header}" add="${attrs.add}" minimum="${attrs.minimum ?: 0}" enableTopButton="${attrs.enableTopButton}">
-    <div style="width:100%">
-      <st:include page="config.jelly" class="${descriptor.clazz}" />
-      <d:invokeBody/>
-    </div>
+    <st:include page="config.jelly" class="${descriptor.clazz}" />
+    <d:invokeBody/>
   </f:repeatable>
 </j:jelly>
diff --git a/src/main/js/components/dropdowns/hetero-list.js b/src/main/js/components/dropdowns/hetero-list.js
index 0eab2b9ea324..3d8a4684d8dd 100644
--- a/src/main/js/components/dropdowns/hetero-list.js
+++ b/src/main/js/components/dropdowns/hetero-list.js
@@ -151,7 +151,6 @@ function generateButtons() {
             }
             Behaviour.applySubtree(nc, true);
             ensureVisible(nc);
-            nc.classList.remove("fade-in");
             layoutUpdateCallback.call();
           },
           true,
diff --git a/src/main/js/sortable-drag-drop.js b/src/main/js/sortable-drag-drop.js
index e056919c24b5..5724538dbadd 100644
--- a/src/main/js/sortable-drag-drop.js
+++ b/src/main/js/sortable-drag-drop.js
@@ -17,7 +17,30 @@ function registerSortableDragDrop(e) {
     return false;
   }
 
+  let initialX, currentItem;
+  const maxRotation = 2; // Maximum rotation in degrees
+  const maxDistance = 150; // Maximum distance for the full rotation effect
+
+  function onPointerMove(evt) {
+    if (!currentItem) {
+      return;
+    }
+
+    const currentX = evt.clientX + window.scrollX;
+    const distanceX = currentX - initialX - 20;
+
+    // Calculate rotation angle based on the distance moved
+    const rotation = Math.max(
+      -maxRotation,
+      Math.min(maxRotation, (distanceX / maxDistance) * maxRotation),
+    );
+
+    currentItem.style.rotate = `${rotation}deg`;
+    currentItem.style.translate = distanceX * -0.75 + "px";
+  }
+
   new Sortable(e, {
+    animation: 200,
     draggable: ".repeated-chunk",
     handle: ".dd-handle",
     ghostClass: "repeated-chunk--sortable-ghost",
@@ -25,13 +48,18 @@ function registerSortableDragDrop(e) {
     forceFallback: true, // Do not use html5 drag & drop behaviour because it does not work with autoscroll
     scroll: true,
     bubbleScroll: true,
-    onChoose: function (event) {
-      const draggableDiv = event.item;
-      const height = draggableDiv.clientHeight;
-      draggableDiv.style.height = `${height}px`;
+    onStart: function (evt) {
+      const rect = evt.item.getBoundingClientRect();
+      initialX = rect.left + window.scrollX;
+      currentItem = document.querySelector(".sortable-drag");
+      document.addEventListener("pointermove", onPointerMove);
     },
-    onUnchoose: function (event) {
-      event.item.style.removeProperty("height");
+    onEnd: function () {
+      document.removeEventListener("pointermove", onPointerMove);
+      if (currentItem) {
+        currentItem.style.rotate = "";
+        currentItem = null;
+      }
     },
   });
 }
diff --git a/src/main/scss/abstracts/_mixins.scss b/src/main/scss/abstracts/_mixins.scss
index 7999284e1a96..fcdf10ed357a 100644
--- a/src/main/scss/abstracts/_mixins.scss
+++ b/src/main/scss/abstracts/_mixins.scss
@@ -61,6 +61,10 @@
   z-index: 0;
   text-decoration: none !important;
   border-radius: 0.66rem;
+  cursor: pointer;
+  border: none;
+  outline: none;
+  background: transparent;
 
   &::before,
   &::after {
@@ -74,7 +78,7 @@
   }
 
   &::before {
-    background-color: transparent;
+    background-color: var(--item-background);
   }
 
   &::after {
diff --git a/src/main/scss/form/_reorderable-list.scss b/src/main/scss/form/_reorderable-list.scss
index 7cd726556df1..d1b536f19e2a 100644
--- a/src/main/scss/form/_reorderable-list.scss
+++ b/src/main/scss/form/_reorderable-list.scss
@@ -1,22 +1,229 @@
-/* ========================= repeatable elements ========================= */
+@use "../abstracts/mixins";
+
+$inset: 1rem;
+$exit-animation: 0.2s;
 
 .repeated-chunk {
   position: relative;
-  border: 2px dashed var(--input-border);
-  padding: 1rem;
-  border-radius: 10px;
-  margin-bottom: 1rem;
-  margin-top: 1rem;
+  display: flex;
+  flex-direction: column;
+  gap: 0.5rem;
+  background: var(--card-background);
+  border-radius: calc(var(--form-input-border-radius) / 2);
   transition:
-    opacity 0.2s ease-in,
-    max-height 0.2s ease-in;
+    max-height #{$exit-animation} ease,
+    border-radius var(--standard-transition),
+    box-shadow var(--standard-transition);
+  height: unset !important;
+  margin: 0 0 var(--card-border-width) 0;
+
+  &::after {
+    content: "";
+    position: absolute;
+    inset: 0;
+    border: var(--card-border-width) solid var(--card-border-color);
+    border-radius: inherit;
+    pointer-events: none;
+  }
+
+  &:first-of-type {
+    border-top-left-radius: var(--form-input-border-radius);
+    border-top-right-radius: var(--form-input-border-radius);
+  }
+
+  &:last-of-type {
+    border-bottom-left-radius: var(--form-input-border-radius);
+    border-bottom-right-radius: var(--form-input-border-radius);
+  }
+
+  &__header {
+    position: relative;
+    display: flex;
+    align-items: center;
+    justify-content: flex-start;
+    font-weight: var(--form-label-font-weight);
+    min-height: 46px;
+
+    .dd-handle {
+      position: relative;
+      width: 44px;
+      height: 46px;
+      cursor: move;
+      opacity: 0.75;
+      color: var(--text-color-secondary);
+      transition: var(--standard-transition);
+      margin-right: -2px;
+
+      &::after {
+        content: "";
+        position: absolute;
+        inset: 0;
+        background-color: currentColor;
+        mask-image: url("data:image/svg+xml,%3Csvg width='8' height='13' viewBox='0 0 8 13' fill='none' xmlns='http://www.w3.org/2000/svg'%3E%3Cg clip-path='url(%23clip0_0_12)'%3E%3Ccircle cx='1.5' cy='1.5' r='1' stroke='black'/%3E%3Ccircle cx='6.5' cy='1.5' r='1' stroke='black'/%3E%3Ccircle cx='1.5' cy='6.5' r='1' stroke='black'/%3E%3Ccircle cx='6.5' cy='6.5' r='1' stroke='black'/%3E%3Ccircle cx='1.5' cy='11.5' r='1' stroke='black'/%3E%3Ccircle cx='6.5' cy='11.5' r='1' stroke='black'/%3E%3C/g%3E%3Cdefs%3E%3CclipPath id='clip0_0_12'%3E%3Crect width='8' height='13' fill='white'/%3E%3C/clipPath%3E%3C/defs%3E%3C/svg%3E%0A");
+        mask-position: center;
+        mask-repeat: no-repeat;
+      }
+
+      &:hover {
+        opacity: 1;
+        color: var(--text-color);
+      }
+    }
+
+    &--no-handle {
+      padding-left: $inset;
+    }
+  }
+
+  .repeatable-delete {
+    @include mixins.item;
+
+    --item-background: color-mix(in sRGB, currentColor 7.5%, transparent);
+    --item-background--hover: color-mix(in sRGB, currentColor 15%, transparent);
+    --item-background--active: color-mix(
+      in sRGB,
+      currentColor 25%,
+      transparent
+    );
+    --item-box-shadow--focus: color-mix(
+      in sRGB,
+      currentColor 7.5%,
+      transparent
+    );
+
+    position: absolute;
+    top: 0.5rem;
+    right: 0.5rem;
+    display: grid;
+    place-items: center;
+    place-content: center;
+    width: 30px;
+    height: 30px;
+    margin-left: auto;
+    color: var(--red);
+    padding: 0;
+    transition: var(--standard-transition);
+    font-size: 0.65rem;
+
+    &::before,
+    &::after {
+      inset: 4px;
+      border-radius: 0.5rem;
+    }
+
+    &::before {
+      border: 1px solid color-mix(in sRGB, currentColor 2.5%, transparent);
+    }
+
+    // Center and overlap SVG and text content
+    * {
+      grid-area: container;
+    }
+
+    svg {
+      width: 0.875rem;
+      height: 0.875rem;
+      transition: var(--standard-transition);
+
+      * {
+        stroke-width: 40px;
+      }
+    }
+
+    span {
+      opacity: 0;
+      transition: var(--standard-transition);
+      filter: blur(2px);
+      scale: 0.5;
+      text-wrap: nowrap;
+    }
+
+    &:hover,
+    &:active,
+    &:focus {
+      // This value is set in Jelly - see repeatableDeleteButton.jelly
+      width: var(--width);
+
+      &::before,
+      &::after {
+        border-radius: 1rem;
+      }
+
+      svg {
+        opacity: 0;
+        filter: blur(2px);
+        scale: 0.6;
+        rotate: -90deg;
+      }
+
+      span {
+        opacity: 1;
+        filter: none;
+        scale: 1;
+      }
+    }
+  }
+}
+
+@keyframes repeated-chunk-entrance-animation {
+  from {
+    scale: 0.99;
+    opacity: 0;
+    filter: blur(1px);
+  }
+}
+
+@keyframes repeated-chunk-exit-animation {
+  to {
+    scale: 0.98;
+    opacity: 0;
+    filter: blur(3px);
+    translate: 0 -10%;
+  }
+}
+
+.repeated-chunk.fade-in {
+  animation: repeated-chunk-entrance-animation 0.3s both;
 }
 
-.repeated-chunk.fade-in,
 .repeated-chunk.fade-out {
-  opacity: 0;
+  z-index: -10;
+  animation: repeated-chunk-exit-animation #{$exit-animation} both;
 }
 
+.repeated-chunk--sortable-chosen {
+  width: 100%;
+  height: 100px;
+  box-shadow: 0 15px 30px rgb(0 0 20 / 0.05);
+  opacity: 1 !important;
+  backdrop-filter: blur(20px);
+  border-radius: var(--form-input-border-radius) !important;
+  z-index: 10;
+}
+
+.repeated-chunk--sortable-ghost {
+  opacity: 0 !important;
+}
+
+.jenkins-repeated-chunk__content {
+  padding: 0 $inset $inset;
+
+  &:empty {
+    display: none;
+  }
+
+  & > *:last-of-type {
+    margin-bottom: 0;
+  }
+}
+
+.repeated-chunk + .repeatable-insertion-point + .hetero-list-add {
+  margin-top: 1rem;
+  transition: none;
+}
+
+/* ========================= repeatable elements ========================= */
+
 .repeated-chunk .show-if-last {
   visibility: hidden;
 }
@@ -99,143 +306,3 @@
 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(--accent-color);
-
-  & > * {
-    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: 30px;
-      height: 30px;
-      overflow: hidden;
-      margin-right: 0.75rem;
-      cursor: move;
-      margin-left: -6px;
-
-      &::before {
-        content: "";
-        position: absolute;
-        inset: 0;
-        background: var(--text-color);
-        border-radius: var(--form-input-border-radius);
-        opacity: 0;
-        transition: var(--standard-transition);
-      }
-
-      &::after {
-        content: "";
-        position: absolute;
-        inset: 0 4px;
-        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 {
-        &::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;
-      inset: 0;
-      background: currentColor;
-      border-radius: 100px;
-      z-index: -1;
-      opacity: 0.075;
-      transition: var(--standard-transition);
-    }
-
-    &::after {
-      content: "";
-      position: absolute;
-      inset: 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;
-      }
-    }
-
-    &:active,
-    &:focus {
-      &::before {
-        opacity: 0.15;
-      }
-
-      &::after {
-        box-shadow: 0 0 0 5px var(--red);
-      }
-    }
-  }
-}