diff --git a/frontend/src/features/admin-form/create/builder-and-design/MagicFormBuilderModal/MagicFormBuilderModalContent/PdfDetailsScreen.tsx b/frontend/src/features/admin-form/create/builder-and-design/MagicFormBuilderModal/MagicFormBuilderModalContent/PdfDetailsScreen.tsx
index c51f7f1ea8..396141daa0 100644
--- a/frontend/src/features/admin-form/create/builder-and-design/MagicFormBuilderModal/MagicFormBuilderModalContent/PdfDetailsScreen.tsx
+++ b/frontend/src/features/admin-form/create/builder-and-design/MagicFormBuilderModal/MagicFormBuilderModalContent/PdfDetailsScreen.tsx
@@ -86,8 +86,6 @@ export const MagicFormBuilderPdfDetailsScreen = (): JSX.Element => {
     return combinedText.trim()
   }
 
-  const isError = pdfFileText.length > 3000
-
   return (
     <>
       <ModalHeader color="secondary.700">
@@ -97,7 +95,7 @@ export const MagicFormBuilderPdfDetailsScreen = (): JSX.Element => {
       </ModalHeader>
       <ModalBody whiteSpace="pre-wrap">
         <Container maxW={'42.5rem'} p={0}>
-          <FormControl isInvalid={isError || !!errors.pdfFileText}>
+          <FormControl isInvalid={!!errors.pdfFileText}>
             <FormLabel>
               Upload a PDF - The PDF should not be a scanned copy and should not
               contain any restricted or sensitive information.
@@ -105,7 +103,7 @@ export const MagicFormBuilderPdfDetailsScreen = (): JSX.Element => {
             <Controller
               rules={{
                 validate: (pdfFileText) => {
-                  if (pdfFileText && pdfFileText.length < 3001) return true
+                  if (pdfFileText) return true
                   return 'This PDF file cannot be processed. Please ensure that the PDF uploaded contains selectable text and is not a scanned copy.'
                 },
               }}
@@ -127,15 +125,11 @@ export const MagicFormBuilderPdfDetailsScreen = (): JSX.Element => {
             />
 
             <FormErrorMessage alignItems="top">
-              {(isError || !pdfFileText) && (
-                <FormErrorIcon h="1.5rem" as={BxsErrorCircle} />
-              )}
+              {!pdfFileText && <FormErrorIcon h="1.5rem" as={BxsErrorCircle} />}
               {!pdfFileText &&
                 (pdfFile
                   ? `${errors.pdfFileText?.message}`
                   : 'Please upload a PDF.')}
-              {isError &&
-                `The PDF uploaded exceeds the character limit acceptable (${pdfFileText.length}/3000). Please try another form.`}
             </FormErrorMessage>
           </FormControl>
 
diff --git a/src/app/modules/form/admin-form/admin-form.assistance.constants.ts b/src/app/modules/form/admin-form/admin-form.assistance.constants.ts
index 921435bfc7..c35006f106 100644
--- a/src/app/modules/form/admin-form/admin-form.assistance.constants.ts
+++ b/src/app/modules/form/admin-form/admin-form.assistance.constants.ts
@@ -6,3 +6,5 @@ export enum Roles {
 export const MODEL_TYPE = 'gpt-3.5-turbo'
 
 export const sampleFormFields = `[{"title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"section"},{"ValidationOptions":{"selectedValidation":null,"customVal":null},"allowPrefill":"<boolean>","lockPrefill":"<boolean>","title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"textfield"},{"ValidationOptions":{"selectedValidation":null,"customVal":null},"title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"textarea"},{"fieldOptions":["<string>"],"othersRadioButton":"<boolean>","title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"radiobutton"},{"ValidationOptions":{"customMax":null,"customMin":null},"fieldOptions":["<string>"],"othersRadioButton":"<boolean>","validateByValue":"<boolean>","title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"checkbox"},{"fieldOptions":["<string>"],"title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"dropdown"},{"title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"yes_no"},{"ratingOptions":{"steps":5,"shape":"Star"},"title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"rating"},{"autoReplyOptions":{"hasAutoReply":"<boolean>","autoReplySubject":"<string>","autoReplySender":"<string>","autoReplyMessage":"<string>","includeFormSummary":"<boolean>"},"isVerifiable":"<boolean>","hasAllowedEmailDomains":false,"allowedEmailDomains":[],"title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"email"},{"allowIntlNumbers":"<boolean>","isVerifiable":"<boolean>","title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"mobile"},{"allowIntlNumbers":"<boolean>","title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"homeno"},{"dateValidation":{"customMinDate":null,"customMaxDate":null,"selectedDateValidation":null},"invalidDays":[],"title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"date"},{"addMoreRows":"<boolean>","title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"table","columns":[{"ValidationOptions":{"customVal":null,"selectedValidation":null},"allowPrefill":"<boolean>","lockPrefill":"<boolean>","columnType":"textfield","required":"<boolean>","title":"<string>"}],"minimumRows":2,"maximumRows":null},{"title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"attachment","attachmentSize":"1"},{"title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"number","ValidationOptions":{"LengthValidationOptions":{"customVal":null,"selectedLengthValidation":null},"RangeValidationOptions":{"customMin":null,"customMax":null},"selectedValidation":null}},{"ValidationOptions":{"customMax":null,"customMin":null},"validateByValue":"<boolean>","title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"decimal"},{"title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"nric"},{"title":"<string>","description":"<string>","required":"<boolean>","disabled":"<boolean>","fieldType":"uen"}]`
+
+export const fieldTypes = `'section','textfield','textarea','radiobutton','checkbox','dropdown','yes_no','rating','email','mobile','homeno','date','table','attachment','number','decimal','nric','uen'`
diff --git a/src/app/modules/form/admin-form/admin-form.assistance.controller.ts b/src/app/modules/form/admin-form/admin-form.assistance.controller.ts
index ff2bba3d7c..4536d956b6 100644
--- a/src/app/modules/form/admin-form/admin-form.assistance.controller.ts
+++ b/src/app/modules/form/admin-form/admin-form.assistance.controller.ts
@@ -21,10 +21,9 @@ const generateQuestionsSchema = Joi.object({
   type: Joi.string()
     .valid(...Object.values(ContentTypes))
     .required(),
-  content: Joi.alternatives().conditional('type', {
+  content: Joi.string().when('type', {
     is: ContentTypes.PROMPT,
     then: Joi.string().max(300).required(),
-    otherwise: Joi.string().max(3000).required(), // max character of 3000 to cater for PDF uploads
   }),
 })
 
diff --git a/src/app/modules/form/admin-form/admin-form.assistance.service.ts b/src/app/modules/form/admin-form/admin-form.assistance.service.ts
index 351b4ad23e..eeed1e2480 100644
--- a/src/app/modules/form/admin-form/admin-form.assistance.service.ts
+++ b/src/app/modules/form/admin-form/admin-form.assistance.service.ts
@@ -111,7 +111,10 @@ export const generateFormFields = (
 > => {
   const messages: ChatRequestMessage[] = [
     { role: Roles.SYSTEM, content: schemaPromptBuilder(sampleFormFields) },
-    { role: Roles.USER, content: formFieldsPromptBuilder(questions) },
+    {
+      role: Roles.USER,
+      content: formFieldsPromptBuilder(questions, sampleFormFields),
+    },
   ]
   return ResultAsync.fromPromise(
     azureOpenAi.getChatCompletions(deploymentId, messages),
@@ -132,6 +135,7 @@ export const generateFormFields = (
     },
   ).andThen((chatCompletions) => {
     const { message } = chatCompletions.choices[0]
+    // const {tokenUsage} = chatCompletions.usage?.totalTokens?
     if (!message) {
       return errAsync(new AssistanceConnectionError())
     }
diff --git a/src/app/modules/form/admin-form/admin-form.assistance.utils.ts b/src/app/modules/form/admin-form/admin-form.assistance.utils.ts
index f7f29b191f..1db29af812 100644
--- a/src/app/modules/form/admin-form/admin-form.assistance.utils.ts
+++ b/src/app/modules/form/admin-form/admin-form.assistance.utils.ts
@@ -1,4 +1,5 @@
 // type guard for OpenAIError
+import { fieldTypes } from './admin-form.assistance.constants'
 import { OpenAIError } from './admin-form.assistance.types'
 
 export function isOpenAIError(error: unknown): error is OpenAIError {
@@ -24,12 +25,12 @@ export const schemaPromptBuilder = (schema: string) => {
 
 export const questionListPromptBuilder = (purpose: string) => {
   return `I am a public officer who wants to create a form that collects ${purpose}.
-  Give me a list of content / questions I should have in my form built with this form builder, in the form of "${expectedQuestionsListFormat}".`
+  Give me a list of content / questions I should have in my form built with this form builder, in the form of "${expectedQuestionsListFormat}", where <answer type> must follow the category of types within ${fieldTypes}. Do not create the question if the <answer type> does not exist in ${fieldTypes}.`
 }
 
-export const formFieldsPromptBuilder = (questions: string) => {
+export const formFieldsPromptBuilder = (questions: string, schema: string) => {
   return `Help me generate a form with the following list of questions: ${questions}
-  Present the questions as FormSG form fields in JSON (list of form field schemas), in the form of "${expectedFormFieldSchemaFormat}" as defined by the system, without any code blocks. Format the JSON as a single line.`
+  Provide the questions as FormSG form fields in JSON format (with the following keys: ${schema}), in the form of "${expectedFormFieldSchemaFormat}" as defined by the system, without any code blocks. Format the JSON as a single line. Ensure the JSON generated only contain fieldTypes of types ${fieldTypes}. Do not create any fieldTypes which are not ${fieldTypes}. Replace values in <> with actual primitive values. Do not build the fieldType if a path required is not available.`
 }
 export const migratePromptBuilder = (parsedContent: string) => {
   return `Help me generate the corresponding JSON form fields from content parsed from a PDF document.