How to use Chat to PDF for iMessage
Chat to PDF for iMessage
Turn on Full Disk Access or open a copy of a Messages folder, pick a conversation, the dates and your name, and save a PDF with every message, the photos and page numbers.
Free to read. You can explore the guide before buying the app.
On this page
Install Chat to PDF for iMessage
Chat to PDF for iMessage runs on macOS 14 Sonoma or later, on Apple silicon and Intel Macs. After buying, download the app zip from your Polar receipt, unzip it, and drag Chat to PDF for iMessage to your Applications folder.
The app is signed and notarized by Apple. Confirm Open at the normal first-launch prompt.
The app works without a license key. The key in your receipt turns on automatic updates: enter it in Chat to PDF for iMessage → License…. Once a day, the app checks for a new version, shows what’s new, and installs it with Install and Relaunch. Chat to PDF for iMessage → Check for Updates… checks right away. A key works on 3 Macs. To move it to another Mac, choose License… → Deactivate This Mac first. Your receipt always has the latest version, too.
Let the app read your messages
Your Mac keeps the Messages history in a protected folder, in your home folder under Library → Messages. To read it, the app needs Full Disk Access. macOS never asks for it with a prompt: you turn it on yourself, once.
When the app can’t read the history, its window says “Let the app read your messages” and shows three steps:
- Click Open System Settings. It opens Privacy & Security → Full Disk Access.
- Find Chat to PDF for iMessage in the list and turn it on. Your Mac asks for your password. If the app isn’t in the list, click + under the list, pick Chat to PDF for iMessage in Applications and click Open. You can also drag the app’s icon from its window into the list.
- Come back to the app. While the window says “Waiting for Full Disk Access…”, it checks every two seconds and shows your conversations as soon as it can read them. If it doesn’t, quit the app and open it again.
The app only reads. It never changes, moves or deletes a message. You can turn Full Disk Access off again once your PDFs are saved.
Use a copy instead
Click Open a Messages Folder… (or File → Open a Messages Folder…, ⌘O) and pick a copy of a Messages folder, from another Mac or a backup: the one with a file called chat.db in it. A copy doesn’t need Full Disk Access.
You can also pick chat.db itself, or a folder that has Messages or Library/Messages inside. The photos are found inside the copy, in its Attachments folder.
If there’s no Messages history on this Mac, the window says “There are no messages on this Mac” and offers Open a Messages Folder….
The conversations
The app makes a copy of the Messages history in a temporary folder and reads the copy, so Messages can keep running. The window says “Reading your messages…” for a moment, then lists the conversations, the newest first. Each one has the people in it, the day of the last message and how many messages it has. Type in Search to find one by name, number or email address.
An iMessage conversation and a text message (SMS) conversation with the same number are one conversation, as in Messages. A group with no name is called by the people in it, like “Marco Bellini, Sofia Lange and 2 others”.
Pick a conversation and it shows as bubbles, with a heading for each day. Yours are on the right.
Choose what goes in
On top of the conversation:
| Choice | What it does |
|---|---|
| From and To | The first and last day to include, both included whole. They start at the conversation’s first and last message. The line on the right says how many messages are in these dates. |
| Your name | The name on your messages in the PDF. It starts as “You”. |
| Paper | A4 or Letter. |
| Text size | Small, Medium or Large. |
| Photos and videos | On, photos and the first frame of each video are printed in their bubble. Off, each is a line with its file name. |
| Reactions | On, a reaction is a small line under the message, like “Anna loved this”. Off, reactions are left out. |
| Seconds | Times with seconds, like “9:03:12 PM”. |
Names
Messages keeps phone numbers and email addresses, not names. Click Names… to give each one a name. The conversation you picked comes first in the list.
Click Use Names from Contacts and macOS asks whether the app can read your contacts. Click Allow. The app fills in every name it finds, matching numbers saved with or without the country code, and says how many it found, like “Contacts had 3 of 4 names. Type the others here.” A name you typed stays as you typed it.
If you click Don’t Allow, the sheet says “The app isn’t allowed to read Contacts.” Open Contacts Settings opens the place to turn it on. Or type the names by hand.
The app remembers the names for next time.
Save the PDF
Click Save PDF… (⌘S) and pick a name and a folder. The name starts as the conversation’s name, like “Anna Rossi.pdf”. If a file with that name is there, macOS asks whether to replace it.
The window shows “Saving the PDF…” with a progress bar. Cancel stops it, and nothing is left behind.
Then it says what was saved, like “Anna Rossi.pdf: 41 pages, 1,284 messages, 87 photos and 4 videos.”, and what the PDF shows as a line instead of a picture, and why:
- “3 attachments were never downloaded to this Mac. Each one is a line with its file name.”
- “6 voice messages and other files are lines with their names: a PDF can’t hold them.”
- “2 messages have nothing this app can show, like items from iMessage apps, and are left out.”
Show in Finder shows the PDF. The PDF is opened again before the window says it’s saved, so a PDF the app calls saved is a PDF that opens.
What’s in the PDF
The first page has the conversation’s name, then:
| People | The people in the conversation, and your name |
| Dates | The first and last day of the messages in the PDF |
| Messages | How many messages, not counting the lines from Messages itself |
| Made on | The day you made the PDF |
Then the messages, with a heading for each day, like “Saturday, 14 March 2026”. Each bubble has the sender’s name and the time.
- Photos are inside their bubble, at a size that prints sharp.
- A video is its first frame with a play sign, and its file name under it.
- A voice message or another file is a line like “Audio: Audio Message.caf”.
- A photo or video that’s only in iCloud is a line like “Photo: IMG_0413.HEIC. It was never downloaded to this Mac.”
- Reactions are a small line under the message: “Anna loved this”, “Sam laughed at this”, “Sofia reacted with 🥾”, “Anna added a sticker”. A reaction someone took back isn’t there.
- An edited message has “Edited” under it. An unsent message says “This message was unsent.” with “Unsent” under it.
- Lines from Messages itself, like “Anna Rossi added Sofia Lange to the conversation.” or “Marco Bellini named the conversation “Hiking club”.”, are centered in grey.
Every page has, at the bottom, the conversation’s name, the day the PDF was made, and “Page 3 of 41”. You can select and copy the text in the PDF, and search it in Preview.
Privacy
Everything stays on your Mac. The app reads the Messages history from a copy in a temporary folder, and deletes the copy when you quit or open another folder. It never changes anything in Messages, and nothing is uploaded. Contacts is read only after you click Use Names from Contacts, and only to show names.
Once a day the app sends its license key to my update server, updates.flaviocopes.com, to check for a new version, and about once a week it checks the key with Polar, the shop. There are no accounts and no analytics.
Troubleshooting
It’s still waiting for Full Disk Access
Check that the switch next to Chat to PDF for iMessage is on in Privacy & Security → Full Disk Access. Then quit the app and open it again.
The photos are missing
If you use Messages in iCloud, your Mac may keep some photos only in iCloud. Open the conversation in Messages and scroll through it, so the Mac downloads them, then save the PDF again.
It says “This version of macOS isn’t supported yet”
The app checks that the Messages history has everything it reads before it shows anything. When macOS stores messages in a way the app doesn’t know, it stops there, so no PDF has wrong dates or missing messages. An update to the app fixes it.
It says the history can’t be opened
The file may be damaged, or the copy incomplete. Copy the whole Messages folder again, with every file in it, and open the new copy.
Chat to PDF for iMessage isn’t made by, affiliated with or endorsed by Apple. iMessage, Messages and iCloud are trademarks of Apple Inc., used here only to say what the app works with.
See Chat to PDF for iMessage → · $20 including tax.