diff --git a/apps/web/src/app/(signing)/sign/[token]/text-field.tsx b/apps/web/src/app/(signing)/sign/[token]/text-field.tsx
index d324a50ba..50a65f4b4 100644
--- a/apps/web/src/app/(signing)/sign/[token]/text-field.tsx
+++ b/apps/web/src/app/(signing)/sign/[token]/text-field.tsx
@@ -107,7 +107,7 @@ export const TextField = ({ field, recipient }: TextFieldProps) => {
 
       toast({
         title: 'Error',
-        description: 'An error occurred while removing the signature.',
+        description: 'An error occurred while removing the text.',
         variant: 'destructive',
       });
     }
@@ -134,7 +134,7 @@ export const TextField = ({ field, recipient }: TextFieldProps) => {
           </DialogTitle>
 
           <div className="">
-            <Label htmlFor="signature">Custom Text</Label>
+            <Label htmlFor="custom-text">Custom Text</Label>
 
             <Textarea
               id="custom-text"
diff --git a/packages/lib/server-only/pdf/insert-field-in-pdf.ts b/packages/lib/server-only/pdf/insert-field-in-pdf.ts
index dde46ba6b..1aabf96b8 100644
--- a/packages/lib/server-only/pdf/insert-field-in-pdf.ts
+++ b/packages/lib/server-only/pdf/insert-field-in-pdf.ts
@@ -1,3 +1,4 @@
+// https://github.com/Hopding/pdf-lib/issues/20#issuecomment-412852821
 import fontkit from '@pdf-lib/fontkit';
 import { PDFDocument, StandardFonts } from 'pdf-lib';
 
@@ -73,13 +74,17 @@ export const insertFieldInPDF = async (pdf: PDFDocument, field: FieldWithSignatu
       height: imageHeight,
     });
   } else {
-    let textWidth = font.widthOfTextAtSize(field.customText, fontSize);
+    const longestLineInTextForWidth = field.customText
+      .split('\n')
+      .sort((a, b) => b.length - a.length)[0];
+
+    let textWidth = font.widthOfTextAtSize(longestLineInTextForWidth, fontSize);
     const textHeight = font.heightAtSize(fontSize);
 
     const scalingFactor = Math.min(fieldWidth / textWidth, fieldHeight / textHeight, 1);
 
     fontSize = Math.max(Math.min(fontSize * scalingFactor, maxFontSize), minFontSize);
-    textWidth = font.widthOfTextAtSize(field.customText, fontSize);
+    textWidth = font.widthOfTextAtSize(longestLineInTextForWidth, fontSize);
 
     const textX = fieldX + (fieldWidth - textWidth) / 2;
     let textY = fieldY + (fieldHeight - textHeight) / 2;