Loading Databases Guide

Understanding your options for loading messages in ChatKeepsake

ChatKeepsake offers several ways to load your messages, each designed for different scenarios. This guide will help you choose the right method for your needs.

Quick Decision Guide

Your Situation Best Method Why?
Just want to view/export messages from this Mac Reload Mac Messages Fastest, simplest, always up-to-date
Want to edit messages and save changes Mac Messages + Save Copy Start with Mac Messages, then save an editable copy
Need messages from your iPhone (not on Mac) Load iPhone Backup Only way to get iPhone-only messages
Already have an iPhone backup folder Browse for Existing Backup Skips device detection, goes straight to extraction
Previously saved an edited database Open Database... Loads your saved work instantly
Saved database has broken image links Open Database with Attachments... Reconnects database to image folder

All Loading Methods

💬

Reload Mac Messages

File → Reload Mac Messages (⌘R)

Loads messages directly from your Mac's Messages app database. This is the default and recommended method for most users.

✅ Best for:

  • Viewing current conversations from your Mac
  • Exporting recent messages to PDF or CSV
  • Quick access without any setup
  • Always getting the most up-to-date messages
1
Grant Full Disk Access when prompted (required for security)
2
Messages load automatically from ~/Library/Messages/chat.db
3
View, search, and export your conversations
💡 Tip: This database is read-only. To make edits, use Edit Messages mode and then click "Save Copy" to create an editable version.
📱

Load iPhone BackupPRO

File → Load iPhone Backup... (⌘⇧I)

Creates a new encrypted backup of your iPhone using Finder, then extracts and decrypts the messages database and images.

✅ Best for:

  • Accessing messages that haven't synced to your Mac via iCloud
  • Getting a complete snapshot of all iPhone messages at a specific point in time
  • Creating a permanent archive that won't change
  • Backing up messages before switching phones or restoring
1
Connect your iPhone via USB cable
2
Follow the wizard to create an encrypted backup in Finder
3
Enter your backup password
4
ChatKeepsake extracts messages and images automatically
5
Optionally save the extraction for quick access later
⚠️ Important: The backup process typically takes 5-15 minutes depending on your iPhone's data size. Remember your backup password - you'll need it for extraction!

Why does extraction take so long?

iPhone backup extraction typically takes 10-20 minutes (sometimes longer for backups with many images). Here's what's happening during that time:

  • Decryption key derivation (1-2 minutes): Your backup password is processed through 10 million rounds of PBKDF2 encryption to generate the decryption keys. This intentional slowness protects your backup from brute-force attacks.
  • Manifest database decryption (30-60 seconds): The backup's file catalog must be decrypted to locate your messages and images.
  • Message database extraction (1-2 minutes): The messages database (sms.db) is located, decrypted, and extracted from the encrypted backup.
  • Image extraction (5-15 minutes): Every image in your conversations must be individually located in the manifest, decrypted from the backup, and saved. A typical conversation might have 100-500 images.
  • Database loading (2-5 minutes): Reading thousands of messages from the database and building the conversation list.

✅ Good news: This process only happens once! After extracting, you can save the result and reload it instantly using "Open Database..." (no decryption needed).

📂

Browse for Existing BackupPRO

Shows in iPhone Backup wizard

Load messages from an iPhone backup you've already created (either through Finder previously, or located in your MobileSync folder).

✅ Best for:

  • You already have an iPhone backup folder on your Mac
  • Re-extracting messages from a backup you created earlier
  • Accessing backups from a different Mac (copied via external drive)
  • Skipping the device detection step when your iPhone isn't available
1
Go to File → Load iPhone Backup...
2
Click "Browse for Existing Backup" on the detection screen
3
Navigate to your backup folder (contains Manifest.plist)
4
Enter the backup password and extract messages
💡 Default backup location: ~/Library/Application Support/MobileSync/Backup/[DEVICE_ID]/
💾

Open Database...

File → Open Database... (⌘O)

Opens a previously extracted or edited database file. Perfect for continuing work on edited conversations.

✅ Best for:

  • Loading a database you previously saved using "Save Copy" in Edit Messages mode
  • Re-opening extracted iPhone backups you saved for quick access
  • Continuing edits on a conversation you worked on before
  • Opening databases shared from another Mac
1
Go to File → Open Database... (⌘O)
2
Select your saved database file (usually named chatkeepsake_[name]_edited.db)
3
Database loads with all your previous edits intact
💡 Pro tip: Saved databases from iPhone backups include the extracted images, making future loads much faster than re-extracting.
🔗

Open Database with Attachments...

File → Open Database with Attachments...

Advanced recovery feature that lets you manually reconnect a database to its image folder. Use this when images show as "Couldn't be resolved."

✅ Best for:

  • Fixing databases where images show as "Couldn't be resolved"
  • Recovering edited databases that lost their attachment path
  • Opening databases from another Mac where image paths are different
  • Reconnecting moved or renamed attachment folders
1
Go to File → Open Database with Attachments...
2
First dialog: Select your database file (.db)
3
Second dialog: Select the folder containing images (original backup folder or extracted_sms folder)
4
Database opens with images properly linked
⚠️ Note: You only need this method if images aren't displaying. For normal database loading, use "Open Database..." instead.

Editing and Saving Workflow

When to Save a Copy

Understanding when to save helps you preserve your work and avoid re-extraction:

Scenario 1: Editing Mac Messages

1
Load messages via "Reload Mac Messages"
2
Open a conversation and click "Edit Messages"
3
Delete unwanted messages
4
Choose one:
  • Apply Changes: Edits are temporary (reset when you close the conversation)
  • Save Copy: Creates a permanent edited database you can re-open later

Scenario 2: Saving iPhone Backup Extraction

1
Complete iPhone backup extraction (can take 10-20 minutes)
2
When prompted, give it a memorable name (e.g., "iPhone Backup Nov 2025")
3
Click "Save" to keep the extraction
4
Next time, use "Open Database..." to load instantly (no re-extraction needed!)
💡 Storage tip: Saved iPhone backup extractions include all images and typically take 500MB - 2GB of space. The database file alone is only 50-200MB but won't include images.

Common Questions

Which method gives me the most complete message history?

iPhone Backup usually has the most complete history, especially for messages that haven't synced to your Mac via iCloud. However, if your Messages are fully synced via iCloud, both methods will show the same conversations.

Can I edit messages from my Mac Messages database?

You can view and export the original Mac Messages database directly, but to make edits, you need to save a copy first. Use Edit Messages mode, make your changes, then click "Save Copy" to create an editable version.

What's the difference between "Apply Changes" and "Save Copy"?

Apply Changes: Your edits are temporary - they only last for the current session. When you close the conversation or quit ChatKeepsake, the edits are lost.

Save Copy: Creates a permanent edited database file. You can re-open this file anytime using "Open Database..." and your edits will be preserved.

Why do some images show as "Couldn't be resolved"?

This happens when the database file can't find the folder containing the images. Common causes:

Solution: Use "Open Database with Attachments..." to manually reconnect the database to its image folder.

Do I need to re-extract my iPhone backup every time?

No! After extracting once, you can save the extraction and use "Open Database..." for instant loading. The extraction process (which takes 10-20 minutes) only needs to happen once per backup.

What's the best workflow for creating a memorial book?

For creating a permanent keepsake:

  1. Use Load iPhone Backup to get the most complete message history
  2. Save the extraction when prompted (so you can make changes later)
  3. Open the conversation and enter Edit Messages mode
  4. Remove any messages you don't want in the book
  5. Click Save Copy to preserve your edits
  6. Export to PDF with binding margin enabled for printing