diff --git a/packages/cli/cli/src/__test__/checkOutputDirectory.test.ts b/packages/cli/cli/src/__test__/checkOutputDirectory.test.ts
index 66dfd102232..d90d072ac17 100644
--- a/packages/cli/cli/src/__test__/checkOutputDirectory.test.ts
+++ b/packages/cli/cli/src/__test__/checkOutputDirectory.test.ts
@@ -4,24 +4,35 @@ import tmp from "tmp-promise";
 import { checkOutputDirectory } from "../commands/generate/checkOutputDirectory";
 import { getOutputDirectories } from "../persistence/getOutputDirectories";
 import { storeOutputDirectories } from "../persistence/storeOutputDirectories";
-import { describe, it, expect, beforeEach, vi, Mock } from "vitest";
+import { describe, it, expect, beforeEach, vi, Mock, afterEach } from "vitest";
+import { CliContext } from "../cli-context/CliContext";
 
 describe("checkOutputDirectory", () => {
     let mockCliContext: {
-        confirmPrompt: Mock;
+        confirmPrompt: Mock & ((message: string, defaultValue?: boolean) => Promise<boolean>);
     };
+    let originalEnv: NodeJS.ProcessEnv;
 
     beforeEach(() => {
         mockCliContext = {
-            confirmPrompt: vi.fn()
+            confirmPrompt: vi.fn().mockImplementation(async () => true)
         };
+        originalEnv = process.env;
+        process.env = {
+            ...process.env,
+            CI: "false"
+        };
+    });
+
+    afterEach(() => {
+        process.env = originalEnv;
     });
 
     it("doesn't prompt if directory doesn't exist", async () => {
         const tmpDir = await tmp.dir();
         const nonExistentPath = join(AbsoluteFilePath.of(tmpDir.path), RelativeFilePath.of("non-existent"));
 
-        const result = await checkOutputDirectory(nonExistentPath, mockCliContext as any, false);
+        const result = await checkOutputDirectory(nonExistentPath, mockCliContext as unknown as CliContext, false);
 
         expect(result).toEqual({
             shouldProceed: true
@@ -34,7 +45,7 @@ describe("checkOutputDirectory", () => {
         const emptyDir = join(AbsoluteFilePath.of(tmpDir.path), RelativeFilePath.of("empty"));
         await mkdir(emptyDir);
 
-        const result = await checkOutputDirectory(emptyDir, mockCliContext as any, false);
+        const result = await checkOutputDirectory(emptyDir, mockCliContext as unknown as CliContext, false);
 
         expect(result).toEqual({
             shouldProceed: true
@@ -50,7 +61,7 @@ describe("checkOutputDirectory", () => {
 
         mockCliContext.confirmPrompt.mockResolvedValueOnce(true);
 
-        const result = await checkOutputDirectory(dirWithFiles, mockCliContext as any, false);
+        const result = await checkOutputDirectory(dirWithFiles, mockCliContext as unknown as CliContext, false);
 
         expect(result).toEqual({
             shouldProceed: true
@@ -67,7 +78,7 @@ describe("checkOutputDirectory", () => {
         // Add to safelist
         await storeOutputDirectories([safelistedDir]);
 
-        const result = await checkOutputDirectory(safelistedDir, mockCliContext as any, false);
+        const result = await checkOutputDirectory(safelistedDir, mockCliContext as unknown as CliContext, false);
 
         expect(result).toEqual({
             shouldProceed: true
@@ -83,7 +94,7 @@ describe("checkOutputDirectory", () => {
 
         mockCliContext.confirmPrompt.mockResolvedValueOnce(true);
 
-        const result = await checkOutputDirectory(dirToSafelist, mockCliContext as any, false);
+        const result = await checkOutputDirectory(dirToSafelist, mockCliContext as unknown as CliContext, false);
 
         expect(result).toEqual({
             shouldProceed: true
@@ -102,7 +113,7 @@ describe("checkOutputDirectory", () => {
 
         mockCliContext.confirmPrompt.mockResolvedValueOnce(false); // overwrite prompt
 
-        const result = await checkOutputDirectory(dirWithFiles, mockCliContext as any, false);
+        const result = await checkOutputDirectory(dirWithFiles, mockCliContext as unknown as CliContext, false);
 
         expect(result).toEqual({
             shouldProceed: false
@@ -116,7 +127,7 @@ describe("checkOutputDirectory", () => {
         await mkdir(dirWithFiles);
         await writeFile(join(dirWithFiles, RelativeFilePath.of("test.txt")), "test");
 
-        const result = await checkOutputDirectory(dirWithFiles, mockCliContext as any, true);
+        const result = await checkOutputDirectory(dirWithFiles, mockCliContext as unknown as CliContext, true);
 
         expect(result).toEqual({ shouldProceed: true });
         expect(mockCliContext.confirmPrompt).not.toHaveBeenCalled();
diff --git a/packages/cli/cli/src/__test__/checkOutputDirectoryCI.test.ts b/packages/cli/cli/src/__test__/checkOutputDirectoryCI.test.ts
index 44e4572d47e..076d252958b 100644
--- a/packages/cli/cli/src/__test__/checkOutputDirectoryCI.test.ts
+++ b/packages/cli/cli/src/__test__/checkOutputDirectoryCI.test.ts
@@ -2,13 +2,12 @@ import { AbsoluteFilePath, join, RelativeFilePath } from "@fern-api/fs-utils";
 import { mkdir, writeFile } from "fs/promises";
 import tmp from "tmp-promise";
 import { checkOutputDirectory } from "../commands/generate/checkOutputDirectory";
-import { describe, it, expect, beforeEach, afterEach, vi, Mock } from "vitest";
+import { describe, it, expect, beforeEach, afterEach, vi } from "vitest";
+import { CliContext } from "../cli-context/CliContext";
 
 describe("checkOutputDirectory in CI", () => {
     let originalEnv: NodeJS.ProcessEnv;
-    let mockCliContext: {
-        confirmPrompt: Mock;
-    };
+    let mockCliContext: Partial<CliContext>;
 
     beforeEach(() => {
         originalEnv = process.env;
@@ -32,7 +31,7 @@ describe("checkOutputDirectory in CI", () => {
         await mkdir(dirWithFiles);
         await writeFile(join(dirWithFiles, RelativeFilePath.of("test.txt")), "test");
 
-        const result = await checkOutputDirectory(dirWithFiles, mockCliContext as any, false);
+        const result = await checkOutputDirectory(dirWithFiles, mockCliContext as CliContext, false);
 
         expect(result).toEqual({
             shouldProceed: true
diff --git a/packages/cli/ete-tests/src/tests/generate/output-directory-prompts.test.ts b/packages/cli/ete-tests/src/tests/generate/output-directory-prompts.test.ts
new file mode 100644
index 00000000000..77f6dff8c36
--- /dev/null
+++ b/packages/cli/ete-tests/src/tests/generate/output-directory-prompts.test.ts
@@ -0,0 +1,43 @@
+import { AbsoluteFilePath, join, RelativeFilePath } from "@fern-api/fs-utils";
+import { cp, mkdir } from "fs/promises";
+import tmp from "tmp-promise";
+import { runFernCli } from "../../utils/runFernCli";
+import stripAnsi from "strip-ansi";
+import { init } from "../init/init";
+import { Options } from "execa";
+
+const envWithCI = {
+    CI: "true"
+};
+
+const envWithoutCI = {
+    CI: "false"
+};
+
+describe("output directory prompts", () => {
+    it("doesn't show prompts for CI environment", async () => {
+        const pathOfDirectory = await init();
+
+        const { stdout } = await runFernCli(["generate", "--local", "--keepDocker"], {
+            cwd: pathOfDirectory,
+            env: envWithCI
+        });
+
+        const cleanOutput = stripAnsi(stdout).trim();
+        expect(cleanOutput).not.toContain("contains existing files");
+        expect(cleanOutput).not.toContain("Would you like to save this");
+    }, 180_000);
+
+    it("doesn't show prompts with the --force flag", async () => {
+        const pathOfDirectory = await init();
+
+        const { stdout } = await runFernCli(["generate", "--local", "--keepDocker", "--force"], {
+            cwd: pathOfDirectory,
+            env: envWithoutCI
+        });
+
+        const cleanOutput = stripAnsi(stdout).trim();
+        expect(cleanOutput).not.toContain("contains existing files");
+        expect(cleanOutput).not.toContain("Would you like to save this");
+    }, 180_000);
+});