diff --git a/packages/calcite-components/src/components.d.ts b/packages/calcite-components/src/components.d.ts
index 071ad829682..af91005d058 100644
--- a/packages/calcite-components/src/components.d.ts
+++ b/packages/calcite-components/src/components.d.ts
@@ -9,7 +9,7 @@ import { Alignment, Appearance, CollapseDirection, FlipContext, IconType, Kind,
 import { RequestedItem } from "./components/accordion/interfaces";
 import { RequestedItem as RequestedItem1 } from "./components/accordion-item/interfaces";
 import { ActionMessages } from "./components/action/assets/action/t9n";
-import { EffectivePlacement, LogicalPlacement, MenuPlacement, OverlayPositioning, ReferenceElement } from "./utils/floating-ui";
+import { FlipPlacement, LogicalPlacement, MenuPlacement, OverlayPositioning, ReferenceElement } from "./utils/floating-ui";
 import { ActionBarMessages } from "./components/action-bar/assets/action-bar/t9n";
 import { Columns } from "./components/action-group/interfaces";
 import { ActionGroupMessages } from "./components/action-group/assets/action-group/t9n";
@@ -100,7 +100,7 @@ export { Alignment, Appearance, CollapseDirection, FlipContext, IconType, Kind,
 export { RequestedItem } from "./components/accordion/interfaces";
 export { RequestedItem as RequestedItem1 } from "./components/accordion-item/interfaces";
 export { ActionMessages } from "./components/action/assets/action/t9n";
-export { EffectivePlacement, LogicalPlacement, MenuPlacement, OverlayPositioning, ReferenceElement } from "./utils/floating-ui";
+export { FlipPlacement, LogicalPlacement, MenuPlacement, OverlayPositioning, ReferenceElement } from "./utils/floating-ui";
 export { ActionBarMessages } from "./components/action-bar/assets/action-bar/t9n";
 export { Columns } from "./components/action-group/interfaces";
 export { ActionGroupMessages } from "./components/action-group/assets/action-group/t9n";
@@ -430,7 +430,7 @@ export namespace Components {
         /**
           * Defines the available placements that can be used when a flip occurs.
          */
-        "flipPlacements": EffectivePlacement[];
+        "flipPlacements": FlipPlacement[];
         /**
           * Specifies the text string for the component.
          */
@@ -1231,7 +1231,7 @@ export namespace Components {
         /**
           * Defines the available placements that can be used when a flip occurs.
          */
-        "flipPlacements": EffectivePlacement[];
+        "flipPlacements": FlipPlacement[];
         /**
           * The `id` of the form that will be associated with the component.  When not set, the component will be associated with its ancestor form element, if any.
          */
@@ -1629,7 +1629,7 @@ export namespace Components {
         /**
           * Defines the available placements that can be used when a flip occurs.
          */
-        "flipPlacements": EffectivePlacement[];
+        "flipPlacements": FlipPlacement[];
         /**
           * Specifies the maximum number of `calcite-dropdown-item`s to display before showing a scroller. Value must be greater than `0`, and does not include `groupTitle`'s from `calcite-dropdown-group`.
          */
@@ -2251,7 +2251,7 @@ export namespace Components {
         /**
           * Defines the available placements that can be used when a flip occurs.
          */
-        "flipPlacements": EffectivePlacement[];
+        "flipPlacements": FlipPlacement[];
         /**
           * When `true`, prevents focus trapping.
          */
@@ -3838,7 +3838,7 @@ export namespace Components {
         /**
           * Defines the available placements that can be used when a flip occurs.
          */
-        "flipPlacements": EffectivePlacement[];
+        "flipPlacements": FlipPlacement[];
         /**
           * When `true`, prevents focus trapping.
          */
@@ -8124,7 +8124,7 @@ declare namespace LocalJSX {
         /**
           * Defines the available placements that can be used when a flip occurs.
          */
-        "flipPlacements"?: EffectivePlacement[];
+        "flipPlacements"?: FlipPlacement[];
         /**
           * Specifies the text string for the component.
          */
@@ -8986,7 +8986,7 @@ declare namespace LocalJSX {
         /**
           * Defines the available placements that can be used when a flip occurs.
          */
-        "flipPlacements"?: EffectivePlacement[];
+        "flipPlacements"?: FlipPlacement[];
         /**
           * The `id` of the form that will be associated with the component.  When not set, the component will be associated with its ancestor form element, if any.
          */
@@ -9427,7 +9427,7 @@ declare namespace LocalJSX {
         /**
           * Defines the available placements that can be used when a flip occurs.
          */
-        "flipPlacements"?: EffectivePlacement[];
+        "flipPlacements"?: FlipPlacement[];
         /**
           * Specifies the maximum number of `calcite-dropdown-item`s to display before showing a scroller. Value must be greater than `0`, and does not include `groupTitle`'s from `calcite-dropdown-group`.
          */
@@ -10065,7 +10065,7 @@ declare namespace LocalJSX {
         /**
           * Defines the available placements that can be used when a flip occurs.
          */
-        "flipPlacements"?: EffectivePlacement[];
+        "flipPlacements"?: FlipPlacement[];
         /**
           * When `true`, prevents focus trapping.
          */
@@ -11749,7 +11749,7 @@ declare namespace LocalJSX {
         /**
           * Defines the available placements that can be used when a flip occurs.
          */
-        "flipPlacements"?: EffectivePlacement[];
+        "flipPlacements"?: FlipPlacement[];
         /**
           * When `true`, prevents focus trapping.
          */
diff --git a/packages/calcite-components/src/components/action-menu/action-menu.tsx b/packages/calcite-components/src/components/action-menu/action-menu.tsx
index 9aef5401634..c49e17b093d 100755
--- a/packages/calcite-components/src/components/action-menu/action-menu.tsx
+++ b/packages/calcite-components/src/components/action-menu/action-menu.tsx
@@ -12,7 +12,7 @@ import {
 import { Fragment, VNode } from "@stencil/core/internal";
 import { getRoundRobinIndex } from "../../utils/array";
 import { focusElement, toAriaBoolean } from "../../utils/dom";
-import { EffectivePlacement, LogicalPlacement, OverlayPositioning } from "../../utils/floating-ui";
+import { FlipPlacement, LogicalPlacement, OverlayPositioning } from "../../utils/floating-ui";
 import { guid } from "../../utils/guid";
 import { isActivationKey } from "../../utils/key";
 import {
@@ -82,7 +82,7 @@ export class ActionMenu implements LoadableComponent {
   /**
    * Defines the available placements that can be used when a flip occurs.
    */
-  @Prop() flipPlacements: EffectivePlacement[];
+  @Prop() flipPlacements: FlipPlacement[];
 
   /**
    *  Specifies the text string for the component.
diff --git a/packages/calcite-components/src/components/combobox/combobox.tsx b/packages/calcite-components/src/components/combobox/combobox.tsx
index 2aa5bc9bb56..4e1a1213b38 100644
--- a/packages/calcite-components/src/components/combobox/combobox.tsx
+++ b/packages/calcite-components/src/components/combobox/combobox.tsx
@@ -20,8 +20,8 @@ import {
   connectFloatingUI,
   defaultMenuPlacement,
   disconnectFloatingUI,
-  EffectivePlacement,
-  filterComputedPlacements,
+  filterValidFlipPlacements,
+  FlipPlacement,
   FloatingCSS,
   FloatingUIComponent,
   LogicalPlacement,
@@ -283,7 +283,7 @@ export class Combobox
   /**
    * Defines the available placements that can be used when a flip occurs.
    */
-  @Prop() flipPlacements: EffectivePlacement[];
+  @Prop() flipPlacements: FlipPlacement[];
 
   /**
    * Made into a prop for testing purposes only
@@ -523,7 +523,7 @@ export class Combobox
 
   placement: LogicalPlacement = defaultMenuPlacement;
 
-  filteredFlipPlacements: EffectivePlacement[];
+  filteredFlipPlacements: FlipPlacement[];
 
   internalValueChangeFlag = false;
 
@@ -629,7 +629,7 @@ export class Combobox
     const { el, flipPlacements } = this;
 
     this.filteredFlipPlacements = flipPlacements
-      ? filterComputedPlacements(flipPlacements, el)
+      ? filterValidFlipPlacements(flipPlacements, el)
       : null;
   };
 
diff --git a/packages/calcite-components/src/components/dropdown/dropdown.tsx b/packages/calcite-components/src/components/dropdown/dropdown.tsx
index ad0a054680e..54ff3aede9c 100644
--- a/packages/calcite-components/src/components/dropdown/dropdown.tsx
+++ b/packages/calcite-components/src/components/dropdown/dropdown.tsx
@@ -16,8 +16,8 @@ import {
   connectFloatingUI,
   defaultMenuPlacement,
   disconnectFloatingUI,
-  EffectivePlacement,
-  filterComputedPlacements,
+  filterValidFlipPlacements,
+  FlipPlacement,
   FloatingCSS,
   FloatingUIComponent,
   MenuPlacement,
@@ -107,7 +107,7 @@ export class Dropdown
   /**
    * Defines the available placements that can be used when a flip occurs.
    */
-  @Prop() flipPlacements: EffectivePlacement[];
+  @Prop() flipPlacements: FlipPlacement[];
 
   @Watch("flipPlacements")
   flipPlacementsHandler(): void {
@@ -421,7 +421,7 @@ export class Dropdown
 
   @Element() el: HTMLCalciteDropdownElement;
 
-  filteredFlipPlacements: EffectivePlacement[];
+  filteredFlipPlacements: FlipPlacement[];
 
   private items: HTMLCalciteDropdownItemElement[] = [];
 
@@ -466,7 +466,7 @@ export class Dropdown
     const { el, flipPlacements } = this;
 
     this.filteredFlipPlacements = flipPlacements
-      ? filterComputedPlacements(flipPlacements, el)
+      ? filterValidFlipPlacements(flipPlacements, el)
       : null;
   };
 
diff --git a/packages/calcite-components/src/components/input-date-picker/input-date-picker.tsx b/packages/calcite-components/src/components/input-date-picker/input-date-picker.tsx
index 156ac9dd9c5..c18ef55a705 100644
--- a/packages/calcite-components/src/components/input-date-picker/input-date-picker.tsx
+++ b/packages/calcite-components/src/components/input-date-picker/input-date-picker.tsx
@@ -28,10 +28,10 @@ import {
   connectFloatingUI,
   defaultMenuPlacement,
   disconnectFloatingUI,
-  EffectivePlacement,
-  filterComputedPlacements,
+  filterValidFlipPlacements,
   FloatingCSS,
   FloatingUIComponent,
+  FlipPlacement,
   MenuPlacement,
   OverlayPositioning,
   reposition,
@@ -201,7 +201,7 @@ export class InputDatePicker
   /**
    * Defines the available placements that can be used when a flip occurs.
    */
-  @Prop() flipPlacements: EffectivePlacement[];
+  @Prop() flipPlacements: FlipPlacement[];
 
   @Watch("flipPlacements")
   flipPlacementsHandler(): void {
@@ -720,7 +720,7 @@ export class InputDatePicker
 
   private dialogId = `date-picker-dialog--${guid()}`;
 
-  filteredFlipPlacements: EffectivePlacement[];
+  filteredFlipPlacements: FlipPlacement[];
 
   private focusOnOpen = false;
 
@@ -814,7 +814,7 @@ export class InputDatePicker
     const { el, flipPlacements } = this;
 
     this.filteredFlipPlacements = flipPlacements
-      ? filterComputedPlacements(flipPlacements, el)
+      ? filterValidFlipPlacements(flipPlacements, el)
       : null;
   };
 
diff --git a/packages/calcite-components/src/components/popover/popover.tsx b/packages/calcite-components/src/components/popover/popover.tsx
index c34fba1339a..03df59e725b 100644
--- a/packages/calcite-components/src/components/popover/popover.tsx
+++ b/packages/calcite-components/src/components/popover/popover.tsx
@@ -16,8 +16,8 @@ import {
   connectFloatingUI,
   defaultOffsetDistance,
   disconnectFloatingUI,
-  EffectivePlacement,
-  filterComputedPlacements,
+  filterValidFlipPlacements,
+  FlipPlacement,
   FloatingCSS,
   FloatingLayout,
   FloatingUIComponent,
@@ -121,7 +121,7 @@ export class Popover
   /**
    * Defines the available placements that can be used when a flip occurs.
    */
-  @Prop() flipPlacements: EffectivePlacement[];
+  @Prop() flipPlacements: FlipPlacement[];
 
   @Watch("flipPlacements")
   flipPlacementsHandler(): void {
@@ -253,7 +253,7 @@ export class Popover
     this.updateFocusTrapElements(),
   );
 
-  filteredFlipPlacements: EffectivePlacement[];
+  filteredFlipPlacements: FlipPlacement[];
 
   @State() effectiveLocale = "";
 
@@ -409,7 +409,7 @@ export class Popover
     const { el, flipPlacements } = this;
 
     this.filteredFlipPlacements = flipPlacements
-      ? filterComputedPlacements(flipPlacements, el)
+      ? filterValidFlipPlacements(flipPlacements, el)
       : null;
   };
 
diff --git a/packages/calcite-components/src/utils/floating-ui.spec.ts b/packages/calcite-components/src/utils/floating-ui.spec.ts
index 6069b8f3350..8562a9f99f9 100644
--- a/packages/calcite-components/src/utils/floating-ui.spec.ts
+++ b/packages/calcite-components/src/utils/floating-ui.spec.ts
@@ -7,8 +7,8 @@ const {
   connectFloatingUI,
   defaultOffsetDistance,
   disconnectFloatingUI,
-  effectivePlacements,
-  filterComputedPlacements,
+  flipPlacements,
+  filterValidFlipPlacements,
   getEffectivePlacement,
   placements,
   positionFloatingUI,
@@ -197,8 +197,8 @@ it("should have correct value for defaultOffsetDistance", () => {
   expect(defaultOffsetDistance).toBe(6);
 });
 
-it("should filter computed placements", () => {
-  expect(new Set(filterComputedPlacements([...placements], document.createElement("div")))).toEqual(
-    new Set(effectivePlacements),
+it("should filter valid placements", () => {
+  expect(new Set(filterValidFlipPlacements([...placements], document.createElement("div")))).toEqual(
+    new Set(flipPlacements),
   );
 });
diff --git a/packages/calcite-components/src/utils/floating-ui.ts b/packages/calcite-components/src/utils/floating-ui.ts
index 9d921f4f100..9bf730b0338 100644
--- a/packages/calcite-components/src/utils/floating-ui.ts
+++ b/packages/calcite-components/src/utils/floating-ui.ts
@@ -91,7 +91,7 @@ export const positionFloatingUI =
       overlayPositioning: Strategy;
       placement: LogicalPlacement;
       flipDisabled?: boolean;
-      flipPlacements?: EffectivePlacement[];
+      flipPlacements?: FlipPlacement[];
       offsetDistance?: number;
       offsetSkidding?: number;
       arrowEl?: SVGElement;
@@ -117,7 +117,7 @@ export const positionFloatingUI =
       middleware: getMiddleware({
         placement,
         flipDisabled,
-        flipPlacements,
+        flipPlacements: flipPlacements?.map((placement) => getEffectivePlacement(floatingEl, placement)),
         offsetDistance,
         offsetSkidding,
         arrowEl,
@@ -244,7 +244,9 @@ export const menuEffectivePlacements: EffectivePlacement[] = [
   "bottom-end",
 ];
 
-export const flipPlacements: EffectivePlacement[] = [
+export type FlipPlacement = Exclude<LogicalPlacement, "auto" | "auto-start" | "auto-end">;
+
+export const flipPlacements: FlipPlacement[] = [
   "top",
   "bottom",
   "right",
@@ -257,6 +259,12 @@ export const flipPlacements: EffectivePlacement[] = [
   "right-end",
   "left-start",
   "left-end",
+  "leading",
+  "trailing",
+  "leading-start",
+  "leading-end",
+  "trailing-start",
+  "trailing-end",
 ];
 
 export type MenuPlacement = Extract<
@@ -374,14 +382,14 @@ function getMiddleware({
   return [];
 }
 
-export function filterComputedPlacements(placements: string[], el: HTMLElement): EffectivePlacement[] {
+export function filterValidFlipPlacements(placements: string[], el: HTMLElement): EffectivePlacement[] {
   const filteredPlacements = placements.filter((placement: EffectivePlacement) =>
-    effectivePlacements.includes(placement),
+    flipPlacements.includes(placement),
   ) as EffectivePlacement[];
 
   if (filteredPlacements.length !== placements.length) {
     console.warn(
-      `${el.tagName}: Invalid value found in: flipPlacements. Try any of these: ${effectivePlacements
+      `${el.tagName}: Invalid value found in: flipPlacements. Try any of these: ${flipPlacements
         .map((placement) => `"${placement}"`)
         .join(", ")
         .trim()}`,