diff --git a/.github/workflows/main.yml b/.github/workflows/main.yml
index 3abb5de5e..cccbf2d05 100644
--- a/.github/workflows/main.yml
+++ b/.github/workflows/main.yml
@@ -289,6 +289,7 @@ jobs:
           - fields-relationship
           - fields__collections__Array
           - fields__collections__Blocks
+          - fields__collections__Checkbox
           - fields__collections__Collapsible
           - fields__collections__ConditionalLogic
           - fields__collections__CustomID
diff --git a/packages/ui/src/elements/WhereBuilder/index.tsx b/packages/ui/src/elements/WhereBuilder/index.tsx
index 4a13a76d0..2d8f83307 100644
--- a/packages/ui/src/elements/WhereBuilder/index.tsx
+++ b/packages/ui/src/elements/WhereBuilder/index.tsx
@@ -174,7 +174,7 @@ export const WhereBuilder: React.FC<WhereBuilderProps> = (props) => {
                         const initialValue =
                           conditions[orIndex].and[andIndex]?.[initialFieldName]?.[
                             initialOperator
-                          ] || ''
+                          ] || undefined
 
                         return (
                           <li key={andIndex}>
diff --git a/test/fields/collections/Checkbox/e2e.spec.ts b/test/fields/collections/Checkbox/e2e.spec.ts
new file mode 100644
index 000000000..3552c0efb
--- /dev/null
+++ b/test/fields/collections/Checkbox/e2e.spec.ts
@@ -0,0 +1,84 @@
+import type { Page } from '@playwright/test'
+
+import { expect, test } from '@playwright/test'
+import path from 'path'
+import { wait } from 'payload/shared'
+import { fileURLToPath } from 'url'
+
+import { ensureCompilationIsDone, initPageConsoleErrorCatch } from '../../../helpers.js'
+import { AdminUrlUtil } from '../../../helpers/adminUrlUtil.js'
+import { initPayloadE2ENoConfig } from '../../../helpers/initPayloadE2ENoConfig.js'
+import { reInitializeDB } from '../../../helpers/reInitializeDB.js'
+import { RESTClient } from '../../../helpers/rest.js'
+import { TEST_TIMEOUT_LONG } from '../../../playwright.config.js'
+import { checkboxFieldsSlug } from '../../slugs.js'
+
+const filename = fileURLToPath(import.meta.url)
+const currentFolder = path.dirname(filename)
+const dirname = path.resolve(currentFolder, '../../')
+
+const { beforeAll, beforeEach, describe } = test
+
+let client: RESTClient
+let page: Page
+let serverURL: string
+let url: AdminUrlUtil
+
+describe('Checkboxes', () => {
+  beforeAll(async ({ browser }, testInfo) => {
+    testInfo.setTimeout(TEST_TIMEOUT_LONG)
+    process.env.SEED_IN_CONFIG_ONINIT = 'false' // Makes it so the payload config onInit seed is not run. Otherwise, the seed would be run unnecessarily twice for the initial test run - once for beforeEach and once for onInit
+    ;({ serverURL } = await initPayloadE2ENoConfig({
+      dirname,
+      // prebuild,
+    }))
+
+    url = new AdminUrlUtil(serverURL, checkboxFieldsSlug)
+
+    const context = await browser.newContext()
+    page = await context.newPage()
+    initPageConsoleErrorCatch(page)
+
+    await ensureCompilationIsDone({ page, serverURL })
+  })
+
+  beforeEach(async () => {
+    await reInitializeDB({
+      serverURL,
+      snapshotKey: 'fieldsTest',
+      uploadsDir: path.resolve(dirname, './collections/Upload/uploads'),
+    })
+    if (client) {
+      await client.logout()
+    }
+    client = new RESTClient(null, { defaultSlug: 'users', serverURL })
+    await client.login()
+    await ensureCompilationIsDone({ page, serverURL })
+  })
+
+  test('should not crash on filtering where checkbox is first field', async () => {
+    await page.goto(url.list)
+
+    const filterButton = page.locator('.list-controls__toggle-where')
+    await filterButton.click()
+
+    const addButton = page.locator('.where-builder__add-first-filter')
+    await addButton.click()
+
+    const operator = page.locator('.condition__operator .rs__control')
+    await operator.click()
+
+    const equals = page.locator('.rs__option:has-text("equals")')
+    await equals.click()
+
+    const value = page.locator('.condition__value')
+    await value.click()
+
+    const trueOption = page.locator('.rs__option:has-text("True")')
+    await trueOption.click()
+
+    await wait(1000)
+
+    await expect(page.locator('table > tbody > tr')).toHaveCount(1)
+  })
+})
diff --git a/test/fields/seed.ts b/test/fields/seed.ts
index 456667995..a114c4e10 100644
--- a/test/fields/seed.ts
+++ b/test/fields/seed.ts
@@ -31,6 +31,7 @@ import { uploadsDoc } from './collections/Upload/shared.js'
 import {
   arrayFieldsSlug,
   blockFieldsSlug,
+  checkboxFieldsSlug,
   codeFieldsSlug,
   collapsibleFieldsSlug,
   collectionSlugs,
@@ -308,6 +309,24 @@ export const seed = async (_payload: Payload) => {
     overrideAccess: true,
   })
 
+  await _payload.create({
+    collection: checkboxFieldsSlug,
+    data: {
+      checkbox: true,
+    },
+    depth: 0,
+    overrideAccess: true,
+  })
+
+  await _payload.create({
+    collection: checkboxFieldsSlug,
+    data: {
+      checkbox: false,
+    },
+    depth: 0,
+    overrideAccess: true,
+  })
+
   await _payload.create({
     collection: codeFieldsSlug,
     data: codeDoc,