diff --git a/apps/remix/app/components/dialogs/sign-field-number-dialog.tsx b/apps/remix/app/components/dialogs/sign-field-number-dialog.tsx
index 3df56b0e4..613bdd1e5 100644
--- a/apps/remix/app/components/dialogs/sign-field-number-dialog.tsx
+++ b/apps/remix/app/components/dialogs/sign-field-number-dialog.tsx
@@ -20,10 +20,15 @@ import { z } from 'zod';
 
 export type SignFieldNumberDialogProps = {
   fieldMeta: TNumberFieldMeta;
+
+  /**
+   * The current value of the field. When set, an empty submit is allowed so the signer can clear the field.
+   */
+  defaultValue?: string;
 };
 
 export const SignFieldNumberDialog = createCallable<SignFieldNumberDialogProps, string | null>(
-  ({ call, fieldMeta }) => {
+  ({ call, fieldMeta, defaultValue }) => {
     const { t } = useLingui();
 
     // Needs to be inside dialog for translation purposes.
@@ -83,14 +88,16 @@ export const SignFieldNumberDialog = createCallable<SignFieldNumberDialogProps,
       });
     };
 
+    const numberSchema = createNumberFieldSchema(fieldMeta);
+
     const ZSignFieldNumberFormSchema = z.object({
-      number: createNumberFieldSchema(fieldMeta),
+      number: defaultValue ? numberSchema.or(z.literal('')) : numberSchema,
     });
 
     const form = useForm<z.infer<typeof ZSignFieldNumberFormSchema>>({
       resolver: zodResolver(ZSignFieldNumberFormSchema),
       defaultValues: {
-        number: undefined,
+        number: defaultValue,
       },
     });
 
diff --git a/apps/remix/app/components/dialogs/sign-field-text-dialog.tsx b/apps/remix/app/components/dialogs/sign-field-text-dialog.tsx
index d651282ed..03d9b64da 100644
--- a/apps/remix/app/components/dialogs/sign-field-text-dialog.tsx
+++ b/apps/remix/app/components/dialogs/sign-field-text-dialog.tsx
@@ -26,75 +26,84 @@ type TSignFieldTextFormSchema = z.infer<typeof ZSignFieldTextFormSchema>;
 
 export type SignFieldTextDialogProps = {
   fieldMeta?: TTextFieldMeta;
+
+  /**
+   * The current value of the field. When set, an empty submit is allowed so the signer can clear the field.
+   */
+  defaultValue?: string;
 };
 
-export const SignFieldTextDialog = createCallable<SignFieldTextDialogProps, string | null>(({ call, fieldMeta }) => {
-  const { t } = useLingui();
+export const SignFieldTextDialog = createCallable<SignFieldTextDialogProps, string | null>(
+  ({ call, fieldMeta, defaultValue }) => {
+    const { t } = useLingui();
 
-  const form = useForm<TSignFieldTextFormSchema>({
-    resolver: zodResolver(ZSignFieldTextFormSchema),
-    defaultValues: {
-      text: '',
-    },
-  });
+    const form = useForm<TSignFieldTextFormSchema>({
+      resolver: zodResolver(defaultValue ? z.object({ text: z.string() }) : ZSignFieldTextFormSchema),
+      defaultValues: {
+        text: defaultValue ?? '',
+      },
+    });
 
-  return (
-    <Dialog open={true} onOpenChange={(value) => (!value ? call.end(null) : null)}>
-      <DialogContent>
-        <DialogHeader>
-          <DialogTitle>{fieldMeta?.label || <Trans>Enter Text</Trans>}</DialogTitle>
+    return (
+      <Dialog open={true} onOpenChange={(value) => (!value ? call.end(null) : null)}>
+        <DialogContent>
+          <DialogHeader>
+            <DialogTitle>{fieldMeta?.label || <Trans>Enter Text</Trans>}</DialogTitle>
 
-          <DialogDescription className="mt-4">
-            <Trans>Please enter a value</Trans>
-          </DialogDescription>
-        </DialogHeader>
+            <DialogDescription className="mt-4">
+              <Trans>Please enter a value</Trans>
+            </DialogDescription>
+          </DialogHeader>
 
-        <Form {...form}>
-          <form onSubmit={form.handleSubmit((data) => call.end(data.text))}>
-            <fieldset className="flex h-full flex-col space-y-4" disabled={form.formState.isSubmitting}>
-              <FormField
-                control={form.control}
-                name="text"
-                render={({ field, fieldState }) => (
-                  <FormItem>
-                    <FormControl>
-                      <Textarea
-                        id="custom-text"
-                        placeholder={fieldMeta?.placeholder ?? t`Enter your text here`}
-                        className={cn('w-full rounded-md', {
-                          'border-2 border-red-300 text-left ring-2 ring-red-200 ring-offset-2 ring-offset-red-200 focus-visible:border-red-400 focus-visible:ring-4 focus-visible:ring-red-200 focus-visible:ring-offset-2 focus-visible:ring-offset-red-200':
-                            fieldState.error,
-                        })}
-                        {...field}
-                      />
-                    </FormControl>
-                    <FormMessage />
-                    {fieldMeta?.characterLimit !== undefined && fieldMeta?.characterLimit > 0 && !fieldState.error && (
-                      <div className="text-muted-foreground text-sm">
-                        <Plural
-                          value={fieldMeta?.characterLimit - (field.value?.length ?? 0)}
-                          one="# character remaining"
-                          other="# characters remaining"
+          <Form {...form}>
+            <form onSubmit={form.handleSubmit((data) => call.end(data.text))}>
+              <fieldset className="flex h-full flex-col space-y-4" disabled={form.formState.isSubmitting}>
+                <FormField
+                  control={form.control}
+                  name="text"
+                  render={({ field, fieldState }) => (
+                    <FormItem>
+                      <FormControl>
+                        <Textarea
+                          id="custom-text"
+                          placeholder={fieldMeta?.placeholder ?? t`Enter your text here`}
+                          className={cn('w-full rounded-md', {
+                            'border-2 border-red-300 text-left ring-2 ring-red-200 ring-offset-2 ring-offset-red-200 focus-visible:border-red-400 focus-visible:ring-4 focus-visible:ring-red-200 focus-visible:ring-offset-2 focus-visible:ring-offset-red-200':
+                              fieldState.error,
+                          })}
+                          {...field}
                         />
-                      </div>
-                    )}
-                  </FormItem>
-                )}
-              />
+                      </FormControl>
+                      <FormMessage />
+                      {fieldMeta?.characterLimit !== undefined &&
+                        fieldMeta?.characterLimit > 0 &&
+                        !fieldState.error && (
+                          <div className="text-muted-foreground text-sm">
+                            <Plural
+                              value={fieldMeta?.characterLimit - (field.value?.length ?? 0)}
+                              one="# character remaining"
+                              other="# characters remaining"
+                            />
+                          </div>
+                        )}
+                    </FormItem>
+                  )}
+                />
 
-              <DialogFooter>
-                <Button type="button" variant="secondary" onClick={() => call.end(null)}>
-                  <Trans>Cancel</Trans>
-                </Button>
+                <DialogFooter>
+                  <Button type="button" variant="secondary" onClick={() => call.end(null)}>
+                    <Trans>Cancel</Trans>
+                  </Button>
 
-                <Button type="submit">
-                  <Trans>Enter</Trans>
-                </Button>
-              </DialogFooter>
-            </fieldset>
-          </form>
-        </Form>
-      </DialogContent>
-    </Dialog>
-  );
-});
+                  <Button type="submit">
+                    <Trans>Enter</Trans>
+                  </Button>
+                </DialogFooter>
+              </fieldset>
+            </form>
+          </Form>
+        </DialogContent>
+      </Dialog>
+    );
+  },
+);
diff --git a/apps/remix/app/utils/field-signing/number-field.ts b/apps/remix/app/utils/field-signing/number-field.ts
index c866317bf..0be6ed2f5 100644
--- a/apps/remix/app/utils/field-signing/number-field.ts
+++ b/apps/remix/app/utils/field-signing/number-field.ts
@@ -21,27 +21,22 @@ export const handleNumberFieldClick = async (
     });
   }
 
-  if (field.inserted) {
-    return {
-      type: FieldType.NUMBER,
-      value: null,
-    };
-  }
-
   let numberToInsert = number;
 
   if (!numberToInsert) {
     numberToInsert = await SignFieldNumberDialog.call({
       fieldMeta: field.fieldMeta,
+      defaultValue: field.inserted ? field.customText : undefined,
     });
   }
 
-  if (!numberToInsert) {
+  if (numberToInsert === null) {
     return null;
   }
 
+  // An empty value clears the field.
   return {
     type: FieldType.NUMBER,
-    value: numberToInsert,
+    value: numberToInsert || null,
   };
 };
diff --git a/apps/remix/app/utils/field-signing/text-field.ts b/apps/remix/app/utils/field-signing/text-field.ts
index 48873faee..0aad18559 100644
--- a/apps/remix/app/utils/field-signing/text-field.ts
+++ b/apps/remix/app/utils/field-signing/text-field.ts
@@ -21,27 +21,22 @@ export const handleTextFieldClick = async (
     });
   }
 
-  if (field.inserted) {
-    return {
-      type: FieldType.TEXT,
-      value: null,
-    };
-  }
-
   let textToInsert = text;
 
   if (!textToInsert) {
     textToInsert = await SignFieldTextDialog.call({
       fieldMeta: field.fieldMeta,
+      defaultValue: field.inserted ? field.customText : undefined,
     });
   }
 
-  if (!textToInsert) {
+  if (textToInsert === null) {
     return null;
   }
 
+  // An empty value clears the field.
   return {
     type: FieldType.TEXT,
-    value: textToInsert,
+    value: textToInsert || null,
   };
 };
diff --git a/packages/app-tests/e2e/envelopes/envelope-v2-field-insertion.spec.ts b/packages/app-tests/e2e/envelopes/envelope-v2-field-insertion.spec.ts
index 741111bbd..07cdbd244 100644
--- a/packages/app-tests/e2e/envelopes/envelope-v2-field-insertion.spec.ts
+++ b/packages/app-tests/e2e/envelopes/envelope-v2-field-insertion.spec.ts
@@ -5,7 +5,7 @@ import { expect, test } from '@playwright/test';
 import { DocumentStatus, FieldType } from '@prisma/client';
 import { DateTime } from 'luxon';
 
-import { apiSeedPendingDocument } from '../fixtures/api-seeds';
+import { apiSeedPendingDocument, apiSeedTemplate } from '../fixtures/api-seeds';
 
 const PDF_PAGE_SELECTOR = 'img[data-page-number]';
 
@@ -253,4 +253,81 @@ test.describe('V2 envelope field insertion during signing', () => {
       expect(dbEnvelope.status).toBe(DocumentStatus.COMPLETED);
     }).toPass();
   });
+
+  test('clicking a prefilled text field opens it for editing instead of clearing it', async ({ page, request }) => {
+    const { envelope: template, token: apiToken } = await apiSeedTemplate(request, {
+      recipients: [{ email: 'prefill-signer@test.documenso.com', name: 'Prefill Signer' }],
+      fieldsPerRecipient: [
+        [
+          {
+            type: FieldType.TEXT,
+            page: 1,
+            positionX: 10,
+            positionY: 10,
+            width: 20,
+            height: 5,
+            fieldMeta: { type: 'text', label: 'Mailing Address' },
+          },
+          { type: FieldType.SIGNATURE, page: 1, positionX: 10, positionY: 30, width: 20, height: 5 },
+        ],
+      ],
+    });
+
+    const [templateRecipient] = template.recipients;
+    const templateField = template.fields.find((field) => field.type === FieldType.TEXT);
+
+    if (!templateField) {
+      throw new Error('Text field not found');
+    }
+
+    const formData = new FormData();
+
+    formData.append(
+      'payload',
+      JSON.stringify({
+        envelopeId: template.id,
+        recipients: [{ id: templateRecipient.id, email: templateRecipient.email, name: templateRecipient.name }],
+        prefillFields: [{ id: templateField.id, type: 'text', label: 'Mailing Address', value: '144 Plymouth' }],
+        distributeDocument: true,
+      }),
+    );
+
+    const useResponse = await request.post('/api/v2/envelope/use', {
+      headers: { Authorization: `Bearer ${apiToken}` },
+      multipart: formData,
+    });
+
+    expect(useResponse.ok(), await useResponse.text()).toBeTruthy();
+
+    const { id: envelopeId } = await useResponse.json();
+
+    const recipient = await prisma.recipient.findFirstOrThrow({ where: { envelopeId } });
+
+    await page.goto(`/sign/${recipient.token}`);
+    await expect(page.locator(PDF_PAGE_SELECTOR).first()).toBeVisible({ timeout: 30_000 });
+
+    const canvas = page.locator('.konva-container canvas').first();
+    await expect(canvas).toBeVisible({ timeout: 30_000 });
+
+    const canvasBox = await canvas.boundingBox();
+
+    if (!canvasBox) {
+      throw new Error('Canvas bounding box not found');
+    }
+
+    await canvas.click({ position: { x: 0.2 * canvasBox.width, y: 0.125 * canvasBox.height } });
+
+    const textInput = page.getByRole('dialog').getByRole('textbox');
+    await expect(textInput).toHaveValue('144 Plymouth');
+
+    await textInput.fill('145 Plymouth');
+    await page.getByRole('button', { name: 'Enter' }).click();
+
+    await expect(async () => {
+      const field = await prisma.field.findFirstOrThrow({ where: { envelopeId, type: FieldType.TEXT } });
+
+      expect(field.inserted).toBe(true);
+      expect(field.customText).toBe('145 Plymouth');
+    }).toPass();
+  });
 });