diff --git a/packages/cli/src/setup-agents.ts b/packages/cli/src/setup-agents.ts
index 6a9721b9..36ff659e 100644
--- a/packages/cli/src/setup-agents.ts
+++ b/packages/cli/src/setup-agents.ts
@@ -1,7 +1,7 @@
 import { mkdir, readFile, rm, writeFile } from 'node:fs/promises';
 import { dirname, join, relative, resolve } from 'node:path';
 import { fileURLToPath } from 'node:url';
-import { cancel, isCancel, multiselect, select } from '@clack/prompts';
+import { cancel, confirm, isCancel, multiselect, select } from '@clack/prompts';
 import {
   loadKtxProject,
   markKtxSetupStateStepComplete,
@@ -277,12 +277,23 @@ function createPromptAdapter(): KtxSetupAgentsPromptAdapter {
       return String(value);
     },
     async multiselect(options) {
-      const value = await withSetupInterruptConfirmation(() => multiselect(withMenuOptionsSpacing(options)));
-      if (isCancel(value)) {
-        cancel('Setup cancelled.');
-        return ['back'];
+      while (true) {
+        const value = await withSetupInterruptConfirmation(() => multiselect(withMenuOptionsSpacing(options)));
+        if (isCancel(value)) {
+          cancel('Setup cancelled.');
+          return ['back'];
+        }
+        const selected = [...value] as string[];
+        if (selected.length === 0 && !options.required) {
+          const skipConfirmed = await confirm({ message: 'Nothing selected. Skip this step?', initialValue: false });
+          if (isCancel(skipConfirmed)) {
+            cancel('Setup cancelled.');
+            return ['back'];
+          }
+          if (!skipConfirmed) continue;
+        }
+        return selected;
       }
-      return [...value] as string[];
     },
     cancel(message) {
       cancel(message);
diff --git a/packages/cli/src/setup-databases.ts b/packages/cli/src/setup-databases.ts
index 18ff7e74..caac2841 100644
--- a/packages/cli/src/setup-databases.ts
+++ b/packages/cli/src/setup-databases.ts
@@ -1,5 +1,5 @@
 import { writeFile } from 'node:fs/promises';
-import { cancel, isCancel, multiselect, password, select, text } from '@clack/prompts';
+import { cancel, confirm, isCancel, multiselect, password, select, text } from '@clack/prompts';
 import type { HistoricSqlDialect } from '@ktx/context/ingest';
 import {
   type KtxProjectConnectionConfig,
@@ -203,12 +203,23 @@ function missingConnectionDetailsPrompt(
 function createPromptAdapter(): KtxSetupDatabasesPromptAdapter {
   return {
     async multiselect(options) {
-      const value = await withSetupInterruptConfirmation(() => multiselect(withMenuOptionsSpacing(options)));
-      if (isCancel(value)) {
-        cancel('Setup cancelled.');
-        return ['back'];
+      while (true) {
+        const value = await withSetupInterruptConfirmation(() => multiselect(withMenuOptionsSpacing(options)));
+        if (isCancel(value)) {
+          cancel('Setup cancelled.');
+          return ['back'];
+        }
+        const selected = [...value] as string[];
+        if (selected.length === 0 && !options.required) {
+          const skipConfirmed = await confirm({ message: 'Nothing selected. Skip this step?', initialValue: false });
+          if (isCancel(skipConfirmed)) {
+            cancel('Setup cancelled.');
+            return ['back'];
+          }
+          if (!skipConfirmed) continue;
+        }
+        return selected;
       }
-      return [...value] as string[];
     },
     async select(options) {
       const value = await withSetupInterruptConfirmation(() => select(withMenuOptionsSpacing(options)));
diff --git a/packages/cli/src/setup-sources.ts b/packages/cli/src/setup-sources.ts
index dc010b0a..695fc1c1 100644
--- a/packages/cli/src/setup-sources.ts
+++ b/packages/cli/src/setup-sources.ts
@@ -2,7 +2,7 @@ import { mkdtemp, readdir, readFile, writeFile } from 'node:fs/promises';
 import { tmpdir } from 'node:os';
 import { join, relative, resolve } from 'node:path';
 import { fileURLToPath, pathToFileURL } from 'node:url';
-import { cancel, isCancel, log, multiselect, password, select, text } from '@clack/prompts';
+import { cancel, confirm, isCancel, log, multiselect, password, select, text } from '@clack/prompts';
 import { localConnectionTypeForConfig, resolveNotionAuthToken } from '@ktx/context/connections';
 import { resolveKtxConfigReference } from '@ktx/context/core';
 import {
@@ -136,12 +136,23 @@ const PRIMARY_SOURCE_DRIVERS = new Set([
 function createPromptAdapter(): KtxSetupSourcesPromptAdapter {
   return {
     async multiselect(options) {
-      const value = await withSetupInterruptConfirmation(() => multiselect(withMenuOptionsSpacing(options)));
-      if (isCancel(value)) {
-        cancel('Setup cancelled.');
-        return ['back'];
+      while (true) {
+        const value = await withSetupInterruptConfirmation(() => multiselect(withMenuOptionsSpacing(options)));
+        if (isCancel(value)) {
+          cancel('Setup cancelled.');
+          return ['back'];
+        }
+        const selected = [...value] as string[];
+        if (selected.length === 0 && !options.required) {
+          const skipConfirmed = await confirm({ message: 'Nothing selected. Skip this step?', initialValue: false });
+          if (isCancel(skipConfirmed)) {
+            cancel('Setup cancelled.');
+            return ['back'];
+          }
+          if (!skipConfirmed) continue;
+        }
+        return selected;
       }
-      return [...value] as string[];
     },
     async select(options) {
       const value = await withSetupInterruptConfirmation(() => select(withMenuOptionsSpacing(options)));