diff --git a/change/@microsoft-fast-foundation-015b56ec-8d8e-4573-9572-9822996f1245.json b/change/@microsoft-fast-foundation-015b56ec-8d8e-4573-9572-9822996f1245.json
new file mode 100644
index 00000000000..8b97a828a64
--- /dev/null
+++ b/change/@microsoft-fast-foundation-015b56ec-8d8e-4573-9572-9822996f1245.json
@@ -0,0 +1,7 @@
+{
+  "type": "prerelease",
+  "comment": "comparisons to document.activeElement consider shadowRoot",
+  "packageName": "@microsoft/fast-foundation",
+  "email": "stephcomeau@msn.com",
+  "dependentChangeType": "prerelease"
+}
diff --git a/packages/web-components/fast-foundation/docs/api-report.md b/packages/web-components/fast-foundation/docs/api-report.md
index 3e92a91d4ae..03c8ffc9bdf 100644
--- a/packages/web-components/fast-foundation/docs/api-report.md
+++ b/packages/web-components/fast-foundation/docs/api-report.md
@@ -2363,6 +2363,9 @@ export type GenerateHeaderOptions = ValuesOf<typeof GenerateHeaderOptions>;
 // @public
 export const getDirection: (rootNode: HTMLElement) => Direction;
 
+// @public (undocumented)
+export function getRootActiveElement(element: Element): Element | null;
+
 // @public
 export const hidden = ":host([hidden]){display:none}";
 
diff --git a/packages/web-components/fast-foundation/src/combobox/combobox.ts b/packages/web-components/fast-foundation/src/combobox/combobox.ts
index 68a978eafda..dd037883a64 100644
--- a/packages/web-components/fast-foundation/src/combobox/combobox.ts
+++ b/packages/web-components/fast-foundation/src/combobox/combobox.ts
@@ -6,6 +6,7 @@ import type { FASTListboxOption } from "../listbox-option/listbox-option.js";
 import { DelegatesARIAListbox } from "../listbox/listbox.js";
 import { StartEnd } from "../patterns/start-end.js";
 import type { StartEndOptions } from "../patterns/start-end.js";
+import { getRootActiveElement } from "../utilities/index.js";
 import { applyMixins } from "../utilities/apply-mixins.js";
 import { FormAssociatedCombobox } from "./combobox.form-associated.js";
 import { ComboboxAutocomplete } from "./combobox.options.js";
@@ -337,7 +338,7 @@ export class FASTCombobox extends FormAssociatedCombobox {
      * Overrides: `Listbox.focusAndScrollOptionIntoView`
      */
     protected focusAndScrollOptionIntoView(): void {
-        if (this.contains(document.activeElement)) {
+        if (this.contains(getRootActiveElement(this))) {
             this.control.focus();
             if (this.firstSelectedOption) {
                 requestAnimationFrame(() => {
diff --git a/packages/web-components/fast-foundation/src/data-grid/data-grid-cell.ts b/packages/web-components/fast-foundation/src/data-grid/data-grid-cell.ts
index 030e64c51b7..f2d322fc61b 100644
--- a/packages/web-components/fast-foundation/src/data-grid/data-grid-cell.ts
+++ b/packages/web-components/fast-foundation/src/data-grid/data-grid-cell.ts
@@ -17,6 +17,7 @@ import {
     keyPageUp,
 } from "@microsoft/fast-web-utilities";
 import { isFocusable } from "tabbable";
+import { getRootActiveElement } from "../utilities/index.js";
 import type { ColumnDefinition } from "./data-grid.js";
 import { DataGridCellTypes } from "./data-grid.options.js";
 
@@ -200,7 +201,8 @@ export class FASTDataGridCell extends FASTElement {
     }
 
     public handleFocusout(e: FocusEvent): void {
-        if (this !== document.activeElement && !this.contains(document.activeElement)) {
+        const activeElement: Element | null = getRootActiveElement(this);
+        if (this !== activeElement && !this.contains(activeElement)) {
             this.isActiveCell = false;
         }
     }
@@ -230,7 +232,7 @@ export class FASTDataGridCell extends FASTElement {
             return;
         }
 
-        const rootActiveElement: Element | null = this.getRootActiveElement();
+        const rootActiveElement: Element | null = getRootActiveElement(this);
 
         switch (e.key) {
             case keyEnter:
@@ -292,16 +294,6 @@ export class FASTDataGridCell extends FASTElement {
         }
     }
 
-    private getRootActiveElement(): Element | null {
-        const rootNode = this.getRootNode();
-
-        if (rootNode instanceof ShadowRoot) {
-            return rootNode.activeElement;
-        }
-
-        return document.activeElement;
-    }
-
     private updateCellView(): void {
         this.disconnectCellView();
 
diff --git a/packages/web-components/fast-foundation/src/data-grid/data-grid.ts b/packages/web-components/fast-foundation/src/data-grid/data-grid.ts
index 1b2297f4471..9d505d440a9 100644
--- a/packages/web-components/fast-foundation/src/data-grid/data-grid.ts
+++ b/packages/web-components/fast-foundation/src/data-grid/data-grid.ts
@@ -20,6 +20,7 @@ import {
     keyPageDown,
     keyPageUp,
 } from "@microsoft/fast-web-utilities";
+import { getRootActiveElement } from "../utilities/index.js";
 import type { FASTDataGridCell } from "./data-grid-cell.js";
 import type { FASTDataGridRow } from "./data-grid-row.js";
 import {
@@ -173,12 +174,10 @@ export class FASTDataGrid extends FASTElement {
             if (this.noTabbing) {
                 this.setAttribute("tabIndex", "-1");
             } else {
+                const activeElement: Element | null = getRootActiveElement(this);
                 this.setAttribute(
                     "tabIndex",
-                    this.contains(document.activeElement) ||
-                        this === document.activeElement
-                        ? "-1"
-                        : "0"
+                    this.contains(activeElement) || this === activeElement ? "-1" : "0"
                 );
             }
         }
@@ -908,9 +907,10 @@ export class FASTDataGrid extends FASTElement {
     };
 
     private queueFocusUpdate(): void {
+        const activeElement: Element | null = getRootActiveElement(this);
         if (
             this.isUpdatingFocus &&
-            (this.contains(document.activeElement) || this === document.activeElement)
+            (this.contains(activeElement) || this === activeElement)
         ) {
             return;
         }
diff --git a/packages/web-components/fast-foundation/src/dialog/dialog.ts b/packages/web-components/fast-foundation/src/dialog/dialog.ts
index 26bc77c1b3b..ab27d31fe67 100644
--- a/packages/web-components/fast-foundation/src/dialog/dialog.ts
+++ b/packages/web-components/fast-foundation/src/dialog/dialog.ts
@@ -7,6 +7,7 @@ import {
 } from "@microsoft/fast-element";
 import { keyEscape, keyTab } from "@microsoft/fast-web-utilities";
 import { isTabbable } from "tabbable";
+import { getRootActiveElement } from "../utilities/index.js";
 
 /**
  * A Switch Custom HTML Element.
@@ -274,7 +275,7 @@ export class FASTDialog extends FASTElement {
             // Add an event listener for focusin events if we are trapping focus
             document.addEventListener("focusin", this.handleDocumentFocus);
             Updates.enqueue(() => {
-                if (this.shouldForceFocus(document.activeElement)) {
+                if (this.shouldForceFocus(getRootActiveElement(this))) {
                     this.focusFirstElement();
                 }
             });
diff --git a/packages/web-components/fast-foundation/src/listbox/listbox.ts b/packages/web-components/fast-foundation/src/listbox/listbox.ts
index be57467bf90..4eca9cb0714 100644
--- a/packages/web-components/fast-foundation/src/listbox/listbox.ts
+++ b/packages/web-components/fast-foundation/src/listbox/listbox.ts
@@ -11,6 +11,7 @@ import {
     keyTab,
     uniqueId,
 } from "@microsoft/fast-web-utilities";
+import { getRootActiveElement } from "../utilities/index.js";
 import { FASTListboxOption, isListboxOption } from "../listbox-option/listbox-option.js";
 import { ARIAGlobalStatesAndProperties } from "../patterns/index.js";
 import { applyMixins } from "../utilities/apply-mixins.js";
@@ -198,7 +199,7 @@ export abstract class FASTListbox extends FASTElement {
         // function is typically called from the `openChanged` observer, `DOM.queueUpdate`
         // causes the calls to be grouped into the same frame. To prevent this,
         // `requestAnimationFrame` is used instead of `DOM.queueUpdate`.
-        if (this.contains(document.activeElement) && optionToFocus !== null) {
+        if (this.contains(getRootActiveElement(this)) && optionToFocus !== null) {
             optionToFocus.focus();
             requestAnimationFrame(() => {
                 optionToFocus.scrollIntoView({ block: "nearest" });
@@ -409,7 +410,7 @@ export abstract class FASTListbox extends FASTElement {
      * @internal
      */
     public mousedownHandler(e: MouseEvent): boolean | void {
-        this.shouldSkipFocus = !this.contains(document.activeElement);
+        this.shouldSkipFocus = !this.contains(getRootActiveElement(this));
         return true;
     }
 
diff --git a/packages/web-components/fast-foundation/src/picker/picker.ts b/packages/web-components/fast-foundation/src/picker/picker.ts
index 769f2ef9465..aae789897bb 100644
--- a/packages/web-components/fast-foundation/src/picker/picker.ts
+++ b/packages/web-components/fast-foundation/src/picker/picker.ts
@@ -32,6 +32,7 @@ import {
     FlyoutPosTop,
     FlyoutPosTopFill,
 } from "../anchored-region/index.js";
+import { getRootActiveElement } from "../utilities/index.js";
 import { FASTPickerListItem } from "./picker-list-item.js";
 import type { FASTPickerList } from "./picker-list.js";
 import { FASTPickerMenuOption } from "./picker-menu-option.js";
@@ -556,7 +557,7 @@ export class FASTPicker extends FormAssociatedPicker {
             return;
         }
 
-        if (open && this.getRootActiveElement() === this.inputElement) {
+        if (open && getRootActiveElement(this) === this.inputElement) {
             this.flyoutOpen = open;
             Updates.enqueue(() => {
                 if (this.menuElement !== undefined) {
@@ -605,7 +606,7 @@ export class FASTPicker extends FormAssociatedPicker {
         if (e.defaultPrevented) {
             return false;
         }
-        const activeElement = this.getRootActiveElement();
+        const activeElement = getRootActiveElement(this);
         switch (e.key) {
             // TODO: what should "home" and "end" keys do, exactly?
             //
@@ -811,7 +812,7 @@ export class FASTPicker extends FormAssociatedPicker {
             this.maxSelected !== 0 &&
             this.selectedItems.length >= this.maxSelected
         ) {
-            if (this.getRootActiveElement() === this.inputElement) {
+            if (getRootActiveElement(this) === this.inputElement) {
                 const selectedItemInstances: Element[] = Array.from(
                     this.listElement.querySelectorAll("[role='listitem']")
                 );
@@ -825,16 +826,6 @@ export class FASTPicker extends FormAssociatedPicker {
         }
     }
 
-    private getRootActiveElement(): Element | null {
-        const rootNode = this.getRootNode();
-
-        if (rootNode instanceof ShadowRoot) {
-            return rootNode.activeElement;
-        }
-
-        return document.activeElement;
-    }
-
     /**
      * A list item has been invoked.
      */
@@ -901,7 +892,7 @@ export class FASTPicker extends FormAssociatedPicker {
             this.listElement.querySelectorAll("[role='listitem']")
         );
 
-        const activeElement = this.getRootActiveElement();
+        const activeElement = getRootActiveElement(this);
         if (activeElement !== null) {
             let currentFocusedItemIndex: number =
                 selectedItemsAsElements.indexOf(activeElement);
diff --git a/packages/web-components/fast-foundation/src/tooltip/tooltip.ts b/packages/web-components/fast-foundation/src/tooltip/tooltip.ts
index 4951f7bda1f..28edc5a93c9 100644
--- a/packages/web-components/fast-foundation/src/tooltip/tooltip.ts
+++ b/packages/web-components/fast-foundation/src/tooltip/tooltip.ts
@@ -9,6 +9,7 @@ import {
     Updates,
 } from "@microsoft/fast-element";
 import { keyEscape, uniqueId } from "@microsoft/fast-web-utilities";
+import { getRootActiveElement } from "../utilities/index.js";
 import { TooltipPlacement } from "./tooltip.options.js";
 
 /**
@@ -171,7 +172,7 @@ export class FASTTooltip extends FASTElement {
      * @internal
      */
     private mouseoverAnchorHandler = (): void => {
-        if (!document.activeElement?.isSameNode(this.anchorElement)) {
+        if (!getRootActiveElement(this)?.isSameNode(this.anchorElement)) {
             this.showTooltip();
         }
     };
@@ -183,7 +184,7 @@ export class FASTTooltip extends FASTElement {
      */
     private mouseoutAnchorHandler = (e: MouseEvent): void => {
         if (
-            !document.activeElement?.isSameNode(this.anchorElement) &&
+            !getRootActiveElement(this)?.isSameNode(this.anchorElement) &&
             !this.isSameNode(e.relatedTarget as HTMLElement)
         ) {
             this.hideTooltip();
diff --git a/packages/web-components/fast-foundation/src/utilities/index.ts b/packages/web-components/fast-foundation/src/utilities/index.ts
index 3acd79ebc11..f9e419f2964 100644
--- a/packages/web-components/fast-foundation/src/utilities/index.ts
+++ b/packages/web-components/fast-foundation/src/utilities/index.ts
@@ -18,3 +18,4 @@ export {
 export { ValuesOf } from "./typings.js";
 export { whitespaceFilter } from "./whitespace-filter.js";
 export { staticallyCompose, StaticallyComposableHTML } from "./template-helpers.js";
+export { getRootActiveElement } from "./root-active-element.js";
diff --git a/packages/web-components/fast-foundation/src/utilities/root-active-element.ts b/packages/web-components/fast-foundation/src/utilities/root-active-element.ts
new file mode 100644
index 00000000000..85999915cbc
--- /dev/null
+++ b/packages/web-components/fast-foundation/src/utilities/root-active-element.ts
@@ -0,0 +1,10 @@
+// returns the active element in the shadow context of the element in question.
+export function getRootActiveElement(element: Element): Element | null {
+    const rootNode = element.getRootNode();
+
+    if (rootNode instanceof ShadowRoot) {
+        return rootNode.activeElement;
+    }
+
+    return document.activeElement;
+}