diff --git a/src/device/webusb.ts b/src/device/webusb.ts
index 3b084f2d8..41f3f2b8f 100644
--- a/src/device/webusb.ts
+++ b/src/device/webusb.ts
@@ -26,6 +26,13 @@ import {
   WebUSBError,
 } from "./device";
 
+// Temporary workaround for ChromeOS 105 bug.
+// See https://bugs.chromium.org/p/chromium/issues/detail?id=1363712&q=usb&can=2
+export const isChromeOS105 = (): boolean => {
+  const userAgent = navigator.userAgent;
+  return /CrOS/.test(userAgent) && /Chrome\/105\b/.test(userAgent);
+};
+
 /**
  * A WebUSB connection to a micro:bit device.
  */
@@ -33,9 +40,10 @@ export class MicrobitWebUSBConnection
   extends EventEmitter
   implements DeviceConnection
 {
-  status: ConnectionStatus = navigator.usb
-    ? ConnectionStatus.NO_AUTHORIZED_DEVICE
-    : ConnectionStatus.NOT_SUPPORTED;
+  status: ConnectionStatus =
+    navigator.usb && !isChromeOS105()
+      ? ConnectionStatus.NO_AUTHORIZED_DEVICE
+      : ConnectionStatus.NOT_SUPPORTED;
 
   /**
    * The USB device we last connected to.
diff --git a/src/workbench/connect-dialogs/WebUSBDialog.tsx b/src/workbench/connect-dialogs/WebUSBDialog.tsx
index ee3ee1fe0..0ab33ce7d 100644
--- a/src/workbench/connect-dialogs/WebUSBDialog.tsx
+++ b/src/workbench/connect-dialogs/WebUSBDialog.tsx
@@ -4,10 +4,12 @@
  * SPDX-License-Identifier: MIT
  */
 import { Button } from "@chakra-ui/button";
-import { HStack, Text, VStack } from "@chakra-ui/react";
-import { useCallback } from "react";
+import { Flex, HStack, Image, Stack, Text, VStack } from "@chakra-ui/react";
+import { ReactNode, useCallback } from "react";
 import { FormattedMessage } from "react-intl";
 import { GenericDialog } from "../../common/GenericDialog";
+import { isChromeOS105 } from "../../device/webusb";
+import chromeOSErrorImage from "./chrome-os-105-error.png";
 
 interface WebUSBDialogProps {
   callback: () => void;
@@ -25,24 +27,32 @@ export const WebUSBDialog = ({
     <GenericDialog
       finalFocusRef={finalFocusRef}
       onClose={handleClose}
-      body={<WebUSBDialogBody />}
+      body={
+        isChromeOS105() ? <Chrome105ErrorBody /> : <NotSupportedErrorBody />
+      }
       footer={<WebUSBDialogFooter onCancel={handleClose} />}
       size="3xl"
     />
   );
 };
 
-const WebUSBDialogBody = () => {
+const DialogBodyWrapper = ({ children }: { children: ReactNode }) => (
+  <VStack
+    width="auto"
+    ml="auto"
+    mr="auto"
+    p={8}
+    pb={0}
+    spacing={5}
+    alignItems="flex-start"
+  >
+    {children}
+  </VStack>
+);
+
+const NotSupportedErrorBody = () => {
   return (
-    <VStack
-      width="auto"
-      ml="auto"
-      mr="auto"
-      p={8}
-      pb={0}
-      spacing={5}
-      alignItems="flex-start"
-    >
+    <DialogBodyWrapper>
       <Text as="h2" fontSize="xl" fontWeight="semibold">
         <FormattedMessage id="webusb-not-supported-title" />
       </Text>
@@ -52,7 +62,43 @@ const WebUSBDialogBody = () => {
       <Text>
         <FormattedMessage id="webusb-why-use" />
       </Text>
-    </VStack>
+    </DialogBodyWrapper>
+  );
+};
+
+const Chrome105ErrorBody = () => {
+  return (
+    <DialogBodyWrapper>
+      <Text as="h2" fontSize="xl" fontWeight="semibold">
+        There is an issue with Chrome OS version 105 and WebUSB*
+      </Text>
+      <HStack spacing={5}>
+        <Stack>
+          <Text>
+            Unfortunately “Send to micro:bit” does not work in this particular
+            Chrome OS version due to a bug in the operating system. The next
+            version of Chrome OS, version 106, expected October 2022, should
+            contain a fix for this.
+          </Text>
+          <Text fontSize="md">
+            Your program will be saved to your computer instead. Follow the
+            steps on the next screen to transfer it to your micro:bit.
+          </Text>
+          <Text fontSize="sm">
+            *<FormattedMessage id="webusb-why-use" />
+          </Text>
+        </Stack>
+        <Flex justifyContent="center" width="100%">
+          <Image
+            width="100%"
+            height="100%"
+            src={chromeOSErrorImage}
+            alt=""
+            pb={3}
+          />
+        </Flex>
+      </HStack>
+    </DialogBodyWrapper>
   );
 };
 
@@ -63,7 +109,7 @@ interface WebUSBDialogFooterProps {
 const WebUSBDialogFooter = ({ onCancel }: WebUSBDialogFooterProps) => {
   return (
     <HStack spacing={2.5}>
-      <Button onClick={onCancel} size="lg">
+      <Button onClick={onCancel} size="lg" variant="solid">
         <FormattedMessage id="close-action" />
       </Button>
     </HStack>
diff --git a/src/workbench/connect-dialogs/chrome-os-105-error.png b/src/workbench/connect-dialogs/chrome-os-105-error.png
new file mode 100644
index 000000000..ac1a26149
Binary files /dev/null and b/src/workbench/connect-dialogs/chrome-os-105-error.png differ