diff --git a/packages/wrangler/package.json b/packages/wrangler/package.json
index 3a945610f1ea..1835021820fb 100644
--- a/packages/wrangler/package.json
+++ b/packages/wrangler/package.json
@@ -109,6 +109,9 @@
           "sourcemap": true
         }
       ]
-    }
+    },
+    "setupFilesAfterEnv": [
+      "<rootDir>/src/__tests__/jest.setup.ts"
+    ]
   }
 }
diff --git a/packages/wrangler/src/__tests__/index.test.ts b/packages/wrangler/src/__tests__/index.test.ts
index 0ac63d7edcae..8461ed433a90 100644
--- a/packages/wrangler/src/__tests__/index.test.ts
+++ b/packages/wrangler/src/__tests__/index.test.ts
@@ -5,41 +5,10 @@ import * as path from "node:path";
 import * as TOML from "@iarna/toml";
 import { main } from "../index";
 import { setMock, unsetAllMocks } from "./mock-cfetch";
-import { confirm } from "../dialogs";
+import { mockConfirm } from "./mock-dialogs";
 
 jest.mock("../cfetch", () => jest.requireActual("./mock-cfetch"));
 
-jest.mock("../dialogs", () => {
-  return {
-    ...jest.requireActual<object>("../dialogs"),
-    confirm: jest
-      .fn()
-      .mockName("confirmMock")
-      .mockImplementation(() => {
-        // By default (if not configured by mockConfirm()) calls to `confirm()` should throw.
-        throw new Error("Unexpected call to `confirm()`.");
-      }),
-  };
-});
-
-/**
- * Mock the implementation of `confirm()` that will respond with configured results
- * for configured confirmation text messages.
- *
- * If there is a call to `confirm()` that does not match any of the expectations
- * then an error is thrown.
- */
-function mockConfirm(...expectations: { text: string; result: boolean }[]) {
-  (confirm as jest.Mock).mockImplementation((text: string) => {
-    for (const { text: expectedText, result } of expectations) {
-      if (text === expectedText) {
-        return result;
-      }
-    }
-    throw new Error(`Unexpected confirmation message: ${text}`);
-  });
-}
-
 async function w(cmd?: string) {
   const logSpy = jest.spyOn(console, "log").mockImplementation();
   const errorSpy = jest.spyOn(console, "error").mockImplementation();
diff --git a/packages/wrangler/src/__tests__/jest.setup.ts b/packages/wrangler/src/__tests__/jest.setup.ts
new file mode 100644
index 000000000000..59b22afddede
--- /dev/null
+++ b/packages/wrangler/src/__tests__/jest.setup.ts
@@ -0,0 +1,17 @@
+import { confirm, prompt } from "../dialogs";
+
+jest.mock("../dialogs");
+
+// By default (if not configured by mockConfirm()) calls to `confirm()` should throw.
+(confirm as jest.Mock).mockImplementation(() => {
+  throw new Error(
+    "Unexpected call to `confirm()`. You should use `mockConfirm()` to mock calls to `confirm()` with expectations. Search the codebase for `mockConfirm` to learn more."
+  );
+});
+
+// By default (if not configured by mockPrompt()) calls to `prompt()` should throw.
+(prompt as jest.Mock).mockImplementation(() => {
+  throw new Error(
+    "Unexpected call to `prompt()`. You should use `mockPrompt()` to mock calls to `prompt()` with expectations. Search the codebase for `mockPrompt` to learn more."
+  );
+});
diff --git a/packages/wrangler/src/__tests__/mock-dialogs.ts b/packages/wrangler/src/__tests__/mock-dialogs.ts
new file mode 100644
index 000000000000..b035675be4fc
--- /dev/null
+++ b/packages/wrangler/src/__tests__/mock-dialogs.ts
@@ -0,0 +1,65 @@
+import { confirm, prompt } from "../dialogs";
+
+/**
+ * The expected values for a confirmation request.
+ */
+export interface ConfirmExpectation {
+  /** The text expected to be seen in the confirmation dialog. */
+  text: string;
+  /** The mock response send back from the confirmation dialog. */
+  result: boolean;
+}
+
+/**
+ * Mock the implementation of `confirm()` that will respond with configured results
+ * for configured confirmation text messages.
+ *
+ * If there is a call to `confirm()` that does not match any of the expectations
+ * then an error is thrown.
+ */
+export function mockConfirm(...expectations: ConfirmExpectation[]) {
+  (confirm as jest.Mock).mockImplementation((text: string) => {
+    for (const { text: expectedText, result } of expectations) {
+      if (text === expectedText) {
+        return Promise.resolve(result);
+      }
+    }
+    throw new Error(`Unexpected confirmation message: ${text}`);
+  });
+}
+
+/**
+ * The expected values for a prompt request.
+ */
+export interface PromptExpectation {
+  /** The text expected to be seen in the prompt dialog. */
+  text: string;
+  /** The type of the prompt. */
+  type: "text" | "password";
+  /** The mock response send back from the prompt dialog. */
+  result: string;
+}
+
+/**
+ * Mock the implementation of `prompt()` that will respond with configured results
+ * for configured prompt text messages.
+ *
+ * If there is a call to `prompt()` that does not match any of the expectations
+ * then an error is thrown.
+ */
+export function mockPrompt(...expectations: PromptExpectation[]) {
+  (prompt as jest.Mock).mockImplementation(
+    (text: string, type: "text" | "password") => {
+      for (const {
+        text: expectedText,
+        type: expectedType,
+        result,
+      } of expectations) {
+        if (text === expectedText && type == expectedType) {
+          return Promise.resolve(result);
+        }
+      }
+      throw new Error(`Unexpected confirmation message: ${text}`);
+    }
+  );
+}