diff --git a/entry_types/scrolled/package/spec/frontend/Layout-spec.js b/entry_types/scrolled/package/spec/frontend/Layout-spec.js
index 4f3f0a1b08..097126b490 100644
--- a/entry_types/scrolled/package/spec/frontend/Layout-spec.js
+++ b/entry_types/scrolled/package/spec/frontend/Layout-spec.js
@@ -10,6 +10,7 @@ import twoColumnStyles from 'frontend/layouts/TwoColumn.module.css';
 import {widthName} from 'frontend/layouts/widths';
 
 import {renderInEntry} from 'testHelpers';
+import {fakeResizeObserver} from 'support/fakeResizeObserver';
 
 describe('Layout', () => {
   describe('placeholder', () => {
@@ -1604,6 +1605,45 @@ describe('Layout', () => {
     });
   });
 
+  describe('sticky box height in two column variant', () => {
+    beforeAll(() => {
+      frontend.contentElementTypes.register('probe', {
+        component: function Probe() {
+          return <div data-testid="probe" />;
+        }
+      });
+    });
+
+    it('exposes observed height of sticky box as custom property', () => {
+      fakeResizeObserver.contentRect = {width: 300, height: 600};
+      const items = [
+        {id: 2, type: 'probe', position: 'sticky'}
+      ];
+      const {getByTestId} = renderInEntry(
+        <Layout sectionProps={{layout: 'left'}} items={items}>
+          {children => children}
+        </Layout>
+      );
+
+      const box = findParentWithClass(getByTestId('probe'), twoColumnStyles.box);
+
+      expect(box.style.getPropertyValue('--sticky-box-height')).toEqual('600px');
+    });
+
+    it('does not observe inline boxes', () => {
+      const items = [
+        {id: 2, type: 'probe', position: 'inline'}
+      ];
+      renderInEntry(
+        <Layout sectionProps={{layout: 'left'}} items={items}>
+          {children => children}
+        </Layout>
+      );
+
+      expect(fakeResizeObserver.observe).not.toHaveBeenCalled();
+    });
+  });
+
   function findParentWithClass(element, className) {
     let currentElement = element;
 
diff --git a/entry_types/scrolled/package/src/frontend/layouts/TwoColumn.js b/entry_types/scrolled/package/src/frontend/layouts/TwoColumn.js
index d3337b56be..bca5d19b2c 100644
--- a/entry_types/scrolled/package/src/frontend/layouts/TwoColumn.js
+++ b/entry_types/scrolled/package/src/frontend/layouts/TwoColumn.js
@@ -1,4 +1,4 @@
-import React, {useCallback, useRef} from 'react';
+import React, {useCallback, useEffect, useRef} from 'react';
 import classNames from 'classnames';
 
 import {api} from '../api';
@@ -97,6 +97,8 @@ function renderItemGroup(props, box, key) {
 function Box({box, children}) {
   const ref = useRef();
 
+  useStickyBoxHeight(ref, box.position === 'sticky');
+
   return (
     <div ref={ref}
          className={classNames(styles.box,
@@ -110,6 +112,28 @@ function Box({box, children}) {
   );
 }
 
+function useStickyBoxHeight(ref, sticky) {
+  useEffect(() => {
+    if (!sticky || typeof ResizeObserver === 'undefined') {
+      return;
+    }
+
+    const box = ref.current;
+
+    const observer = new ResizeObserver(entries =>
+      box.style.setProperty('--sticky-box-height',
+                            `${entries[entries.length - 1].contentRect.height}px`)
+    );
+
+    observer.observe(box);
+
+    return () => {
+      observer.disconnect();
+      box.style.removeProperty('--sticky-box-height');
+    };
+  }, [ref, sticky]);
+}
+
 // Sticky boxes stay pinned while the rest of their group scrolls past.
 // The group therefore is the subject that drives view timelines of
 // content elements inside the box.
diff --git a/entry_types/scrolled/package/src/frontend/layouts/TwoColumn.module.css b/entry_types/scrolled/package/src/frontend/layouts/TwoColumn.module.css
index 3fca9a53b7..59fae58370 100644
--- a/entry_types/scrolled/package/src/frontend/layouts/TwoColumn.module.css
+++ b/entry_types/scrolled/package/src/frontend/layouts/TwoColumn.module.css
@@ -22,6 +22,8 @@
 
 .box {
   max-width: var(--content-max-width);
+  margin-left: calc(var(--side-offset-left, 0px) - var(--margin-to-undo, 0px));
+  margin-right: calc(var(--side-offset-right, 0px) - var(--margin-to-undo, 0px));
 }
 
 .inline {
@@ -103,8 +105,6 @@
   --f: calc(1 / (1 - 2 * var(--content-margin-fraction)));
   --margin-to-undo: var(--theme-content-margin,
                         calc(100% * var(--content-margin-fraction) * var(--f)));
-  margin-left: calc(-1 * var(--margin-to-undo));
-  margin-right: calc(-1 * var(--margin-to-undo));
   max-width: calc(var(--margin-to-undo) * 2 + var(--content-max-width));
 }
 
@@ -117,25 +117,37 @@
   --content-max-width: min(var(--content-width), var(--two-column-sticky-content-max-width, 600px));
   float: right;
   clear: both;
-  top: 33%;
   width: var(--content-width);
 }
 
 .constrainContentWidth .side {
-  position: relative;
   --side-offset: calc((min(var(--layout-inline-content-max-width), var(--constrained-content-max-width, 9999px)) -
                        var(--content-max-width)) / 2);
-  right: var(--side-offset);
+  --side-offset-right: var(--side-offset);
 }
 
 .constrainContentWidth.right .side {
-  right: auto;
-  left: var(--side-offset);
+  --side-offset-right: 0px;
+  --side-offset-left: var(--side-offset);
+}
+
+/*
+  cssnano strips units from zero lengths, turning `0px` into `0`. That
+  would invalidate `initial-value` as well as any zero inside a math
+  function, so the property uses the universal syntax and the box
+  height is clamped to the viewport height instead of the result.
+*/
+@property --sticky-box-height {
+  syntax: '*';
+  inherits: false;
 }
 
 .sticky {
   composes: side;
   position: sticky;
+  --sticky-box-height: 0px;
+  top: min(33%,
+           (100 * var(--vh) - min(var(--sticky-box-height), 100 * var(--vh))) / 2);
 }
 
 .right .side {