diff --git a/apps/marketing/src/app/(marketing)/layout.tsx b/apps/marketing/src/app/(marketing)/layout.tsx
index 4a0c4ccd8..eebb794bb 100644
--- a/apps/marketing/src/app/(marketing)/layout.tsx
+++ b/apps/marketing/src/app/(marketing)/layout.tsx
@@ -9,7 +9,7 @@ export type MarketingLayoutProps = {
 
 export default function MarketingLayout({ children }: MarketingLayoutProps) {
   return (
-    <div className="relative max-w-[100vw] overflow-y-auto overflow-x-hidden pt-20 md:pt-28">
+    <div className="relative max-w-[100vw] pt-20 md:pt-28">
       <div className="fixed left-0 top-0 z-50 w-full bg-white/50 backdrop-blur-md">
         <Header className="mx-auto h-16 max-w-screen-xl px-4 md:h-20 lg:px-8" />
       </div>
diff --git a/apps/marketing/src/app/(marketing)/single-player-mode/page.tsx b/apps/marketing/src/app/(marketing)/single-player-mode/page.tsx
index 0b977d01b..62f8cf265 100644
--- a/apps/marketing/src/app/(marketing)/single-player-mode/page.tsx
+++ b/apps/marketing/src/app/(marketing)/single-player-mode/page.tsx
@@ -204,7 +204,7 @@ export default function SinglePlayerModePage() {
         </div>
 
         <div className="col-span-12 lg:col-span-6 xl:col-span-5">
-          <DocumentFlowFormContainer onSubmit={(e) => e.preventDefault()}>
+          <DocumentFlowFormContainer className="top-24" onSubmit={(e) => e.preventDefault()}>
             <DocumentFlowFormContainerHeader
               title={currentDocumentFlow.title}
               description={currentDocumentFlow.description}
diff --git a/package-lock.json b/package-lock.json
index faaa7705c..41f2648c5 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -19593,7 +19593,7 @@
         "@radix-ui/react-tabs": "^1.0.3",
         "@radix-ui/react-toast": "^1.1.3",
         "@radix-ui/react-toggle": "^1.0.2",
-        "@radix-ui/react-tooltip": "^1.0.5",
+        "@radix-ui/react-tooltip": "^1.0.6",
         "@tanstack/react-table": "^8.9.1",
         "class-variance-authority": "^0.6.0",
         "clsx": "^1.2.1",
diff --git a/packages/ui/package.json b/packages/ui/package.json
index 6b6b6d4a4..3ab123872 100644
--- a/packages/ui/package.json
+++ b/packages/ui/package.json
@@ -24,8 +24,8 @@
     "typescript": "^5.1.6"
   },
   "dependencies": {
-    "@hookform/resolvers": "^3.3.0",
     "@documenso/lib": "*",
+    "@hookform/resolvers": "^3.3.0",
     "@radix-ui/react-accordion": "^1.1.1",
     "@radix-ui/react-alert-dialog": "^1.0.3",
     "@radix-ui/react-aspect-ratio": "^1.0.2",
@@ -51,7 +51,7 @@
     "@radix-ui/react-tabs": "^1.0.3",
     "@radix-ui/react-toast": "^1.1.3",
     "@radix-ui/react-toggle": "^1.0.2",
-    "@radix-ui/react-tooltip": "^1.0.5",
+    "@radix-ui/react-tooltip": "^1.0.6",
     "@tanstack/react-table": "^8.9.1",
     "class-variance-authority": "^0.6.0",
     "clsx": "^1.2.1",
@@ -68,4 +68,4 @@
     "tailwind-merge": "^1.12.0",
     "tailwindcss-animate": "^1.0.5"
   }
-}
\ No newline at end of file
+}
diff --git a/packages/ui/primitives/document-flow/add-signature.tsx b/packages/ui/primitives/document-flow/add-signature.tsx
index ca377b6c8..98164a506 100644
--- a/packages/ui/primitives/document-flow/add-signature.tsx
+++ b/packages/ui/primitives/document-flow/add-signature.tsx
@@ -1,6 +1,6 @@
 'use client';
 
-import { useState } from 'react';
+import { useMemo, useState } from 'react';
 
 import { zodResolver } from '@hookform/resolvers/zod';
 import { DateTime } from 'luxon';
@@ -8,7 +8,7 @@ import { useForm } from 'react-hook-form';
 import { match } from 'ts-pattern';
 
 import { PDF_VIEWER_PAGE_SELECTOR } from '@documenso/lib/constants/pdf-viewer';
-import { FieldType } from '@documenso/prisma/client';
+import { Field, FieldType } from '@documenso/prisma/client';
 import { FieldWithSignature } from '@documenso/prisma/types/field-with-signature';
 import { cn } from '@documenso/ui/lib/utils';
 import { Card, CardContent } from '@documenso/ui/primitives/card';
@@ -24,6 +24,7 @@ import { ElementVisible } from '@documenso/ui/primitives/element-visible';
 import { Input } from '@documenso/ui/primitives/input';
 import { SignaturePad } from '@documenso/ui/primitives/signature-pad';
 
+import { FieldToolTip } from '../field/field-tooltip';
 import { Form, FormControl, FormField, FormItem, FormLabel, FormMessage } from '../form/form';
 import { ZAddSignatureFormSchema } from './add-signature.types';
 import {
@@ -50,6 +51,8 @@ export const AddSignatureFormPartial = ({
   requireName = false,
   requireSignature = true,
 }: AddSignatureFormProps) => {
+  const [validateUninsertedFields, setValidateUninsertedFields] = useState(false);
+
   // Refined schema which takes into account whether to allow an empty name or signature.
   const refinedSchema = ZAddSignatureFormSchema.superRefine((val, ctx) => {
     if (requireName && val.name.length === 0) {
@@ -81,72 +84,101 @@ export const AddSignatureFormPartial = ({
   /**
    * A local copy of the provided fields to modify.
    */
-  const [localFields, setLocalFields] = useState(
-    fields.map((field) => {
-      let customText = field.customText;
+  const [localFields, setLocalFields] = useState<Field[]>(JSON.parse(JSON.stringify(fields)));
 
-      if (field.type === FieldType.DATE) {
-        customText = DateTime.now().toFormat('yyyy-MM-dd hh:mm a');
+  const uninsertedFields = useMemo(() => {
+    const fields = localFields.filter((field) => !field.inserted);
+
+    return fields.sort((a, b) => {
+      if (a.page < b.page) {
+        return -1;
       }
 
-      const inserted = match(field.type)
-        .with(FieldType.DATE, () => true)
-        .with(FieldType.NAME, () => form.getValues('name').length > 0)
-        .with(FieldType.EMAIL, () => form.getValues('email').length > 0)
-        .with(FieldType.SIGNATURE, () => form.getValues('signature').length > 0)
-        .otherwise(() => true);
+      if (a.page > b.page) {
+        return 1;
+      }
 
-      return { ...field, inserted, customText };
-    }),
-  );
+      const aTop = a.positionY;
+      const bTop = b.positionY;
 
-  const onEmailInputBlur = () => {
-    setLocalFields((prev) =>
-      prev.map((field) => {
-        if (field.type !== FieldType.EMAIL) {
-          return field;
-        }
+      if (aTop < bTop) {
+        return -1;
+      }
 
-        const value = form.getValues('email');
+      if (aTop > bTop) {
+        return 1;
+      }
 
-        return {
-          ...field,
-          customText: value,
-          inserted: value.length > 0,
-        };
-      }),
-    );
+      return 0;
+    });
+  }, [localFields]);
+
+  const onValidateFields = async (values: TAddSignatureFormSchema) => {
+    setValidateUninsertedFields(true);
+
+    const firstUninsertedField = uninsertedFields[0];
+
+    const firstUninsertedFieldElement =
+      firstUninsertedField && document.getElementById(`field-${firstUninsertedField.id}`);
+
+    if (firstUninsertedFieldElement) {
+      firstUninsertedFieldElement.scrollIntoView({ behavior: 'smooth', block: 'center' });
+      return;
+    }
+
+    await onSubmit(values);
   };
 
-  const onNameInputBlur = () => {
-    setLocalFields((prev) =>
-      prev.map((field) => {
-        if (field.type !== FieldType.NAME) {
-          return field;
-        }
+  /**
+   * Validates whether the corresponding form for a given field type is valid.
+   *
+   * @returns `true` if the form associated with the provided field is valid, `false` otherwise.
+   */
+  const validateFieldForm = async (fieldType: Field['type']): Promise<boolean> => {
+    if (fieldType === FieldType.SIGNATURE) {
+      await form.trigger('signature');
+      return !form.formState.errors.signature;
+    }
 
-        const value = form.getValues('name');
+    if (fieldType === FieldType.NAME) {
+      await form.trigger('name');
+      return !form.formState.errors.name;
+    }
 
-        return {
-          ...field,
-          customText: value,
-          inserted: value.length > 0,
-        };
-      }),
-    );
+    if (fieldType === FieldType.EMAIL) {
+      await form.trigger('email');
+      return !form.formState.errors.email;
+    }
+
+    return true;
   };
 
-  const onSignatureInputChange = (value: string) => {
-    setLocalFields((prev) =>
-      prev.map((field) => {
-        if (field.type !== FieldType.SIGNATURE) {
-          return field;
-        }
+  /**
+   * Insert the corresponding form value into a given field.
+   */
+  const insertFormValueIntoField = (field: Field) => {
+    return match(field.type)
+      .with(FieldType.DATE, () => ({
+        ...field,
+        customText: DateTime.now().toFormat('yyyy-MM-dd hh:mm a'),
+        inserted: true,
+      }))
+      .with(FieldType.EMAIL, () => ({
+        ...field,
+        customText: form.getValues('email'),
+        inserted: true,
+      }))
+      .with(FieldType.NAME, () => ({
+        ...field,
+        customText: form.getValues('name'),
+        inserted: true,
+      }))
+      .with(FieldType.SIGNATURE, () => {
+        const value = form.getValues('signature');
 
         return {
           ...field,
-          value: value ?? '',
-          inserted: true,
+          value,
           Signature: {
             id: -1,
             recipientId: -1,
@@ -155,7 +187,27 @@ export const AddSignatureFormPartial = ({
             signatureImageAsBase64: value,
             typedSignature: null,
           },
+          inserted: true,
         };
+      })
+      .otherwise(() => {
+        throw new Error('Unsupported field');
+      });
+  };
+
+  const insertField = (field: Field) => async () => {
+    const isFieldFormValid = await validateFieldForm(field.type);
+    if (!isFieldFormValid) {
+      return;
+    }
+
+    setLocalFields((prev) =>
+      prev.map((prevField) => {
+        if (prevField.id !== field.id) {
+          return prevField;
+        }
+
+        return insertFormValueIntoField(field);
       }),
     );
   };
@@ -172,16 +224,7 @@ export const AddSignatureFormPartial = ({
                 <FormItem>
                   <FormLabel required>Email</FormLabel>
                   <FormControl>
-                    <Input
-                      className="bg-background"
-                      type="email"
-                      autoComplete="email"
-                      {...field}
-                      onBlur={() => {
-                        field.onBlur();
-                        onEmailInputBlur();
-                      }}
-                    />
+                    <Input className="bg-background" type="email" autoComplete="email" {...field} />
                   </FormControl>
                   <FormMessage />
                 </FormItem>
@@ -196,14 +239,7 @@ export const AddSignatureFormPartial = ({
                   <FormItem>
                     <FormLabel required={requireName}>Name</FormLabel>
                     <FormControl>
-                      <Input
-                        className="bg-background"
-                        {...field}
-                        onBlur={() => {
-                          field.onBlur();
-                          onNameInputBlur();
-                        }}
-                      />
+                      <Input className="bg-background" {...field} />
                     </FormControl>
                     <FormMessage />
                   </FormItem>
@@ -231,10 +267,7 @@ export const AddSignatureFormPartial = ({
                           <SignaturePad
                             className="h-44 w-full"
                             defaultValue={field.value}
-                            onChange={(value) => {
-                              field.onChange(value ?? '');
-                              onSignatureInputChange(value ?? '');
-                            }}
+                            {...field}
                           />
                         </CardContent>
                       </Card>
@@ -258,19 +291,37 @@ export const AddSignatureFormPartial = ({
             loading={form.formState.isSubmitting}
             disabled={form.formState.isSubmitting}
             onGoBackClick={documentFlow.onBackStep}
-            onGoNextClick={async () => await form.handleSubmit(onSubmit)()}
+            onGoNextClick={form.handleSubmit(onValidateFields)}
           />
         </DocumentFlowFormContainerFooter>
       </fieldset>
 
+      {validateUninsertedFields && uninsertedFields[0] && (
+        <FieldToolTip key={uninsertedFields[0].id} field={uninsertedFields[0]} color="warning">
+          Click to insert field
+        </FieldToolTip>
+      )}
+
       <ElementVisible target={PDF_VIEWER_PAGE_SELECTOR}>
         {localFields.map((field) =>
           match(field.type)
             .with(FieldType.DATE, FieldType.EMAIL, FieldType.NAME, () => {
-              return <SinglePlayerModeCustomTextField key={field.id} field={field} />;
+              return (
+                <SinglePlayerModeCustomTextField
+                  onClick={insertField(field)}
+                  validateUninsertedField={validateUninsertedFields}
+                  key={field.id}
+                  field={field}
+                />
+              );
             })
             .with(FieldType.SIGNATURE, () => (
-              <SinglePlayerModeSignatureField key={field.id} field={field} />
+              <SinglePlayerModeSignatureField
+                onClick={insertField(field)}
+                validateUninsertedField={validateUninsertedFields}
+                key={field.id}
+                field={field}
+              />
             ))
             .otherwise(() => {
               return null;
diff --git a/packages/ui/primitives/document-flow/document-flow-root.tsx b/packages/ui/primitives/document-flow/document-flow-root.tsx
index 300f7d4b3..96a0e18b1 100644
--- a/packages/ui/primitives/document-flow/document-flow-root.tsx
+++ b/packages/ui/primitives/document-flow/document-flow-root.tsx
@@ -21,7 +21,7 @@ export const DocumentFlowFormContainer = ({
     <form
       id={id}
       className={cn(
-        'dark:bg-background border-border bg-widget sticky top-20 flex h-full max-h-[80rem] flex-col rounded-xl border px-4 py-6',
+        'dark:bg-background border-border bg-widget sticky top-20 flex h-full max-h-[64rem] flex-col rounded-xl border px-4 py-6',
         className,
       )}
       {...props}
diff --git a/packages/ui/primitives/document-flow/single-player-mode-fields.tsx b/packages/ui/primitives/document-flow/single-player-mode-fields.tsx
index 2c91bcb88..9c4090cd7 100644
--- a/packages/ui/primitives/document-flow/single-player-mode-fields.tsx
+++ b/packages/ui/primitives/document-flow/single-player-mode-fields.tsx
@@ -28,6 +28,13 @@ export type FieldContainerPortalProps = {
 export type SinglePlayerModeFieldContainerProps = {
   field: FieldWithSignature;
   children: React.ReactNode;
+  validateUninsertedField?: boolean;
+};
+
+export type SinglePlayerModeFieldProps<T> = {
+  field: T;
+  onClick?: () => void;
+  validateUninsertedField?: boolean;
 };
 
 export function FieldContainerPortal({
@@ -56,20 +63,35 @@ export function FieldContainerPortal({
 export function SinglePlayerModeFieldCardContainer({
   field,
   children,
+  validateUninsertedField = false,
 }: SinglePlayerModeFieldContainerProps) {
   return (
     <FieldContainerPortal field={field}>
       <motion.div className="h-full w-full" animate={{ opacity: 1 }} exit={{ opacity: 0 }}>
         <Card
-          className="bg-background relative z-20 h-full w-full"
+          id={`field-${field.id}`}
+          className={cn('bg-background relative z-20 h-full w-full transition-all', {
+            'border-orange-300 ring-1 ring-orange-300': !field.inserted && validateUninsertedField,
+          })}
           data-inserted={field.inserted ? 'true' : 'false'}
         >
-          <CardContent
-            className={cn(
-              'text-foreground hover:shadow-primary-foreground group flex h-full w-full flex-col items-center justify-center p-2',
-            )}
-          >
-            {children}
+          <CardContent className="text-foreground hover:shadow-primary-foreground group flex h-full w-full flex-col items-center justify-center p-2">
+            <AnimatePresence mode="wait" initial={false}>
+              <motion.div
+                key={field.inserted ? 'inserted' : 'not-inserted'}
+                initial={{ opacity: 0 }}
+                animate={{
+                  opacity: 1,
+                }}
+                exit={{ opacity: 0 }}
+                transition={{
+                  duration: 0.2,
+                  ease: 'easeIn',
+                }}
+              >
+                {children}
+              </motion.div>
+            </AnimatePresence>
           </CardContent>
         </Card>
       </motion.div>
@@ -77,7 +99,11 @@ export function SinglePlayerModeFieldCardContainer({
   );
 }
 
-export function SinglePlayerModeSignatureField({ field }: { field: FieldWithSignature }) {
+export function SinglePlayerModeSignatureField({
+  field,
+  validateUninsertedField,
+  onClick,
+}: SinglePlayerModeFieldProps<FieldWithSignature>) {
   const fontVariable = '--font-signature';
   const fontVariableValue = getComputedStyle(document.documentElement).getPropertyValue(
     fontVariable,
@@ -110,50 +136,44 @@ export function SinglePlayerModeSignatureField({ field }: { field: FieldWithSign
   const insertedTypeSignature = field.inserted && field.Signature?.typedSignature;
 
   return (
-    <SinglePlayerModeFieldCardContainer field={field}>
-      <AnimatePresence mode="wait" initial={false}>
-        <motion.div
-          key={
-            (insertedBase64Signature && 'base64Signature') ||
-            (insertedTypeSignature && 'typedSignature') ||
-            'not-inserted'
-          }
-          initial={{ opacity: 0 }}
-          animate={{
-            opacity: 1,
-            transition: {
-              duration: 0.3,
-            },
+    <SinglePlayerModeFieldCardContainer
+      validateUninsertedField={validateUninsertedField}
+      field={field}
+    >
+      {insertedBase64Signature ? (
+        <img
+          src={insertedBase64Signature}
+          alt="Your signature"
+          className="h-full w-full object-contain"
+        />
+      ) : insertedTypeSignature ? (
+        <p
+          ref={$paragraphEl}
+          style={{
+            fontSize: `clamp(${minFontSize}px, ${fontSize}px, ${maxFontSize}px)`,
+            fontFamily: `var(${fontVariable})`,
           }}
-          exit={{ opacity: 0 }}
+          className="font-signature"
         >
-          {insertedBase64Signature ? (
-            <img
-              src={insertedBase64Signature}
-              alt="Your signature"
-              className="h-full w-full object-contain"
-            />
-          ) : insertedTypeSignature ? (
-            <p
-              ref={$paragraphEl}
-              style={{
-                fontSize: `clamp(${minFontSize}px, ${fontSize}px, ${maxFontSize}px)`,
-                fontFamily: `var(${fontVariable})`,
-              }}
-              className="font-signature"
-            >
-              {insertedTypeSignature}
-            </p>
-          ) : (
-            <p className="group-hover:text-primary text-muted-foreground duration-200">Signature</p>
-          )}
-        </motion.div>
-      </AnimatePresence>
+          {insertedTypeSignature}
+        </p>
+      ) : (
+        <button
+          onClick={() => onClick?.()}
+          className="group-hover:text-primary text-muted-foreground absolute inset-0 duration-200"
+        >
+          Signature
+        </button>
+      )}
     </SinglePlayerModeFieldCardContainer>
   );
 }
 
-export function SinglePlayerModeCustomTextField({ field }: { field: Field }) {
+export function SinglePlayerModeCustomTextField({
+  field,
+  validateUninsertedField,
+  onClick,
+}: SinglePlayerModeFieldProps<Field>) {
   const fontVariable = '--font-sans';
   const fontVariableValue = getComputedStyle(document.documentElement).getPropertyValue(
     fontVariable,
@@ -183,7 +203,10 @@ export function SinglePlayerModeCustomTextField({ field }: { field: Field }) {
   const fontSize = maxFontSize * scalingFactor;
 
   return (
-    <SinglePlayerModeFieldCardContainer key="not-inserted" field={field}>
+    <SinglePlayerModeFieldCardContainer
+      validateUninsertedField={validateUninsertedField}
+      field={field}
+    >
       {field.inserted ? (
         <p
           ref={$paragraphEl}
@@ -195,14 +218,17 @@ export function SinglePlayerModeCustomTextField({ field }: { field: Field }) {
           {field.customText}
         </p>
       ) : (
-        <p className="group-hover:text-primary text-muted-foreground text-lg duration-200">
+        <button
+          onClick={() => onClick?.()}
+          className="group-hover:text-primary text-muted-foreground absolute inset-0 text-lg duration-200"
+        >
           {match(field.type)
             .with(FieldType.DATE, () => 'Date')
             .with(FieldType.NAME, () => 'Name')
             .with(FieldType.EMAIL, () => 'Email')
             .with(FieldType.SIGNATURE, FieldType.FREE_SIGNATURE, () => 'Signature')
             .otherwise(() => '')}
-        </p>
+        </button>
       )}
     </SinglePlayerModeFieldCardContainer>
   );
diff --git a/packages/ui/primitives/field/field-tooltip.tsx b/packages/ui/primitives/field/field-tooltip.tsx
new file mode 100644
index 000000000..c2fa9c580
--- /dev/null
+++ b/packages/ui/primitives/field/field-tooltip.tsx
@@ -0,0 +1,63 @@
+import { TooltipArrow } from '@radix-ui/react-tooltip';
+import { VariantProps, cva } from 'class-variance-authority';
+import { createPortal } from 'react-dom';
+
+import { useFieldPageCoords } from '@documenso/lib/client-only/hooks/use-field-page-coords';
+import { cn } from '@documenso/ui/lib/utils';
+import {
+  Tooltip,
+  TooltipContent,
+  TooltipProvider,
+  TooltipTrigger,
+} from '@documenso/ui/primitives/tooltip';
+
+import { Field } from '.prisma/client';
+
+const tooltipVariants = cva('font-semibold', {
+  variants: {
+    color: {
+      default: 'border-2 fill-white',
+      warning: 'border-0 bg-orange-300 fill-orange-300 text-orange-900',
+    },
+  },
+  defaultVariants: {
+    color: 'default',
+  },
+});
+
+interface FieldToolTipProps extends VariantProps<typeof tooltipVariants> {
+  children: React.ReactNode;
+  className?: string;
+  field: Field;
+}
+
+/**
+ * Renders a tooltip for a given field.
+ */
+export function FieldToolTip({ children, color, className = '', field }: FieldToolTipProps) {
+  const coords = useFieldPageCoords(field);
+
+  return createPortal(
+    <div
+      className={cn('absolute', className)}
+      style={{
+        top: `${coords.y}px`,
+        left: `${coords.x}px`,
+        height: `${coords.height}px`,
+        width: `${coords.width}px`,
+      }}
+    >
+      <TooltipProvider>
+        <Tooltip delayDuration={0} open={!field.inserted}>
+          <TooltipTrigger className="absolute top-0 w-full"></TooltipTrigger>
+
+          <TooltipContent className={tooltipVariants({ color, className })} sideOffset={2}>
+            {children}
+            <TooltipArrow />
+          </TooltipContent>
+        </Tooltip>
+      </TooltipProvider>
+    </div>,
+    document.body,
+  );
+}