diff --git a/CHANGELOG.md b/CHANGELOG.md
index bb4a3598f..2b1fa0086 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -209,6 +209,28 @@ Changelog is rather internal in nature. See release notes for the public overvie
 
 ## Version 3.x.x (`release-v3` branch)
 
+- [#586]
+  - **Description:** Adds a new prop `constrainToScrollParent ` to `KDropdownMenu` to allow overriding of its popover flipping behavior.
+  - **Products impact:** Bugfix
+  - **Addresses:** [#432](https://github.com/learningequality/kolibri-design-system/issues/432)
+  - **Components:** KDropdownMenu
+  - **Breaking:** no
+  - **Impacts a11y:**  no
+  - **Guidance:** Use the `constrainToScrollParent` prop to override the default popover flipping behavior of the `KDropdownMenu` component prop where necessary.
+
+[#586]: https://github.com/learningequality/kolibri-design-system/pull/586
+
+- [#573]
+  - **Description:** More precise calculation of list with in KListWithOverflow.
+  - **Products impact:** bugfix.
+  - **Addresses:** -.
+  - **Components:** KListWithOverflow.
+  - **Breaking:** no.
+  - **Impacts a11y:** no.
+  - **Guidance:** -.
+
+[#573]: https://github.com/learningequality/kolibri-design-system/pull/573
+
 - [#552]
   - **Description:** New `KListWithOverflow` component.
   - **Products impact:** new API.
@@ -1382,4 +1404,4 @@ This was the first release of the Design System, with documentation written in a
 
 ## Version 0.1.0
 
-The design system was originally based on a set of internal Kolibri components and their use as documented in the Kolibri Style Guide, which was first introduced into the Kolibri code base [in version 0.6](https://github.com/learningequality/kolibri/tree/release-v0.6.x/kolibri/plugins/style_guide). This remained until [version 0.13](https://github.com/learningequality/kolibri/tree/release-v0.13.x/kolibri/plugins/style_guide) after which the content was migrated to the [current site](https://design-system.learningequality.org/ 'Kolibri Design System Documentation').
+The design system was originally based on a set of internal Kolibri components and their use as documented in the Kolibri Style Guide, which was first introduced into the Kolibri code base [in version 0.6](https://github.com/learningequality/kolibri/tree/release-v0.6.x/kolibri/plugins/style_guide). This remained until [version 0.13](https://github.com/learningequality/kolibri/tree/release-v0.13.x/kolibri/plugins/style_guide) after which the content was migrated to the [current site](https://design-system.learningequality.org/ 'Kolibri Design System Documentation').
\ No newline at end of file
diff --git a/lib/KDropdownMenu.vue b/lib/KDropdownMenu.vue
index 355288e53..824d992c1 100644
--- a/lib/KDropdownMenu.vue
+++ b/lib/KDropdownMenu.vue
@@ -5,6 +5,7 @@
     :z-index="99"
     :containFocus="true"
     :dropdownPosition="position"
+    :constrainToScrollParent="constrainToScrollParent"
     @close="handleClose"
     @open="handleOpen"
   >
@@ -34,6 +35,13 @@
       UiMenu,
     },
     props: {
+      /**
+       * The dropdown menu popover flips its position to avoid overflows within the parent. Setting it to false disables the flipping behavior.
+       */
+      constrainToScrollParent: {
+        type: Boolean,
+        default: true,
+      },
       /**
        * An array of options objects, with one object per dropdown item
        */
diff --git a/lib/KListWithOverflow.vue b/lib/KListWithOverflow.vue
index ee54d69df..db8d852da 100644
--- a/lib/KListWithOverflow.vue
+++ b/lib/KListWithOverflow.vue
@@ -103,26 +103,46 @@
       this.$watch('elementWidth', this.throttledSetOverflowItems);
     },
     methods: {
+      getSize(element) {
+        if (!element) {
+          return { width: 0, height: 0 };
+        }
+        const { width, height } = element.getBoundingClientRect();
+        return { width, height };
+      },
       /**
        * Sets the items that overflow the list, the visibility of the more button,
        * and overrides the `visibility` of the list DOM elements that overflow the list.
        */
       setOverflowItems() {
-        const { list, listWrapper } = this.$refs;
+        const { list, listWrapper, moreButtonWrapper } = this.$refs;
         if (!this.mounted || !listWrapper || !list) {
           this.overflowItems = [];
           return;
         }
 
-        let availableWidth = listWrapper.clientWidth;
+        const newMoreButtonWidth = this.getSize(moreButtonWrapper).width;
+        if (this.isMoreButtonVisible && newMoreButtonWidth > 0) {
+          this.moreButtonWidth = newMoreButtonWidth;
+        }
+
+        let availableWidth = this.getSize(listWrapper).width;
         availableWidth -= this.moreButtonWidth;
         let maxWidth = 0;
         let maxHeight = 0;
 
+        const itemsSizes = [];
+
+        for (let i = 0; i < list.children.length; i++) {
+          const item = list.children[i];
+          const itemSize = this.getSize(item);
+          itemsSizes.push(itemSize);
+        }
+
         const overflowItemsIdx = [];
         for (let i = 0; i < list.children.length; i++) {
           const item = list.children[i];
-          const itemWidth = item.clientWidth;
+          const itemWidth = itemsSizes[i].width;
 
           // If the item dont fit in the available space or if we have already
           // overflowed items, we hide it. This means that once one item overflows,
@@ -134,15 +154,16 @@
             item.style.visibility = 'visible';
             maxWidth += itemWidth;
             availableWidth -= itemWidth;
-            if (item.clientHeight > maxHeight) {
-              maxHeight = item.clientHeight;
+            const itemHeight = itemsSizes[i].height;
+            if (itemHeight > maxHeight) {
+              maxHeight = itemHeight;
             }
           }
         }
 
         // check if overflowed items would fit if the moreButton were not visible
         const overflowedWidth = overflowItemsIdx.reduce(
-          (acc, idx) => acc + list.children[idx].clientWidth,
+          (acc, idx) => acc + itemsSizes[idx].width,
           0
         );
         if (overflowedWidth <= this.moreButtonWidth + availableWidth) {
@@ -150,15 +171,16 @@
             const idx = overflowItemsIdx.pop();
             const item = list.children[idx];
             item.style.visibility = 'visible';
-            maxWidth += item.clientWidth;
+            maxWidth += itemsSizes[idx].width;
           }
         }
 
-        const removedDividerWidth = this.fixDividersVisibility(overflowItemsIdx);
+        const removedDividerWidth = this.fixDividersVisibility(overflowItemsIdx, itemsSizes);
         if (removedDividerWidth) {
           maxWidth -= removedDividerWidth;
         }
 
+        maxWidth = Math.ceil(maxWidth);
         this.overflowItems = overflowItemsIdx.map(idx => this.items[idx]);
         this.isMoreButtonVisible = overflowItemsIdx.length > 0;
         list.style.maxWidth = `${maxWidth}px`;
@@ -169,9 +191,10 @@
        * The visible list should not end with a divider, and the overflowed items should not
        * start with a divider.
        * @param {Array} overflowItemsIdx - The indexes of the items that overflow the list
+       * @param {Array} itemsSizes - The sizes of the items in the list
        * @returns {Number} The width of the removed divider from the visible list, if any
        */
-      fixDividersVisibility(overflowItemsIdx) {
+      fixDividersVisibility(overflowItemsIdx, itemsSizes) {
         if (overflowItemsIdx.length === 0) {
           return;
         }
@@ -186,7 +209,7 @@
         if (this.isDivider(this.items[lastVisibleIdx])) {
           const dividerNode = list.children[lastVisibleIdx];
           dividerNode.style.visibility = 'hidden';
-          return dividerNode.clientWidth;
+          return itemsSizes[lastVisibleIdx].width;
         }
       },
       /**
@@ -201,7 +224,7 @@
         if (!moreButtonWrapper) {
           return;
         }
-        this.moreButtonWidth = moreButtonWrapper.clientWidth;
+        this.moreButtonWidth = this.getSize(moreButtonWrapper).width;
 
         this.isMoreButtonVisible = false;
         moreButtonWrapper.style.visibility = 'visible';