diff --git a/.roo/rules/01-general.md b/.roo/rules/01-general.md
index 9b8d24d..a2a3fdb 100644
--- a/.roo/rules/01-general.md
+++ b/.roo/rules/01-general.md
@@ -13,6 +13,8 @@ Here are special rules you must follow:
 11. Design docs go into docs/design/*.md. These docs are always kept up to date.
 12. Before completing work, ensure that no design docs are left out of sync
 13. Plans go into docs/plans/*.md. These may not be kept in sync, as they are just for brainstorming.
+14. Database migrations are automatically created via `flask db migrate -m 'message'`. NEVER create migrations by hand.
+
 
 # Conventions
 1. modals are rendered server-side, by targeting #modal-holder, and using an hx-trigger response attribute for open-modal.
diff --git a/app/imap_service.py b/app/imap_service.py
index f11452c..72b7947 100644
--- a/app/imap_service.py
+++ b/app/imap_service.py
@@ -3,6 +3,7 @@ import ssl
 import logging
 from typing import List, Dict, Optional, Tuple
 from email.header import decode_header
+from email.utils import parsedate_to_datetime
 from app.models import db, Folder, User
 from app import create_app
 
@@ -173,6 +174,83 @@ class IMAPService:
             self.connection = None
             return 0
     
+    def get_recent_emails(self, folder_name: str, limit: int = 3) -> List[Dict[str, any]]:
+        """Get the most recent email subjects and dates from a specific folder."""
+        try:
+            # Connect to IMAP server
+            self._connect()
+            
+            # Login
+            self.connection.login(
+                self.config.get('username', ''),
+                self.config.get('password', '')
+            )
+            
+            # Select the folder
+            resp_code, content = self.connection.select(folder_name)
+            if resp_code != 'OK':
+                return []
+            
+            # Get email IDs (most recent first)
+            resp_code, content = self.connection.search(None, 'ALL')
+            if resp_code != 'OK':
+                return []
+            
+            # Get the most recent emails (limit to 3)
+            email_ids = content[0].split()
+            recent_email_ids = email_ids[:limit] if len(email_ids) >= limit else email_ids
+            
+            recent_emails = []
+            for email_id in reversed(recent_email_ids):  # Process from newest to oldest
+                # Fetch the email headers
+                resp_code, content = self.connection.fetch(email_id, '(RFC822.HEADER)')
+                if resp_code != 'OK':
+                    continue
+                
+                # Parse the email headers
+                raw_email = content[0][1]
+                import email
+                msg = email.message_from_bytes(raw_email)
+                
+                # Extract subject and date
+                subject = msg.get('Subject', 'No Subject')
+                date_str = msg.get('Date', '')
+                
+                # Decode the subject if needed
+                try:
+                    decoded_parts = decode_header(subject)
+                    subject = ''.join([str(part, encoding or 'utf-8') if isinstance(part, bytes) else part for part, encoding in decoded_parts])
+                except Exception:
+                    pass  # If decoding fails, use the original subject
+                
+                # Parse date if available
+                try:
+                    email_date = parsedate_to_datetime(date_str) if date_str else None
+                except Exception:
+                    email_date = None
+                
+                recent_emails.append({
+                    'subject': subject,
+                    'date': email_date.isoformat() if email_date else None
+                })
+            
+            # Close folder and logout
+            self.connection.close()
+            self.connection.logout()
+            self.connection = None
+            
+            return recent_emails
+            
+        except Exception as e:
+            logging.error(f"Error getting recent emails for folder {folder_name}: {str(e)}")
+            if self.connection:
+                try:
+                    self.connection.logout()
+                except:
+                    pass
+            self.connection = None
+            return []
+    
     def sync_folders(self) -> Tuple[bool, str]:
         """Sync IMAP folders with local database."""
         try:
@@ -215,11 +293,15 @@ class IMAPService:
                     db.session.add(new_folder)
                     synced_count += 1
                 else:
-                    # Update existing folder with email counts
+                    # Update existing folder with email counts and recent emails
                     # Get the total count of emails in this folder
                     total_count = self.get_folder_email_count(folder_name)
                     existing_folder.total_count = total_count
                     existing_folder.pending_count = 0  # Initially set to 0
+                    
+                    # Get the most recent emails for this folder
+                    recent_emails = self.get_recent_emails(folder_name, 3)
+                    existing_folder.recent_emails = recent_emails
             
             db.session.commit()
             return True, f"Successfully synced {synced_count} folders"
diff --git a/app/models.py b/app/models.py
index febf6af..bd8f6b1 100644
--- a/app/models.py
+++ b/app/models.py
@@ -42,5 +42,6 @@ class Folder(Base):
     organize_enabled = db.Column(db.Boolean, default=True)
     total_count = db.Column(db.Integer, default=0)
     pending_count = db.Column(db.Integer, default=0)
+    recent_emails = db.Column(db.JSON, default=list)  # Store recent email subjects with dates
     
     user = db.relationship('User', backref=db.backref('folders', lazy=True))
\ No newline at end of file
diff --git a/app/templates/base.html b/app/templates/base.html
index 740fc87..d4b4034 100644
--- a/app/templates/base.html
+++ b/app/templates/base.html
@@ -10,6 +10,8 @@
     <link href="https://cdn.jsdelivr.net/npm/daisyui@5/themes.css" rel="stylesheet" type="text/css" />
     <link rel="stylesheet" href="https://cdnjs.cloudflare.com/ajax/libs/font-awesome/6.4.0/css/all.min.css">
     <script src="https://cdn.jsdelivr.net/npm/@tailwindcss/browser@4"></script>
+    <script src="https://cdn.jsdelivr.net/npm/@ryangjchandler/alpine-tooltip@1.x.x/dist/cdn.min.js" defer></script>
+    <link rel="stylesheet" href="https://unpkg.com/tippy.js@6/dist/tippy.css" />
     <script defer src="https://cdn.jsdelivr.net/npm/alpinejs@3.x.x/dist/cdn.min.js"></script>
     <style>
         @keyframes shake {
diff --git a/app/templates/partials/folder_card.html b/app/templates/partials/folder_card.html
index 23b9148..9c0a367 100644
--- a/app/templates/partials/folder_card.html
+++ b/app/templates/partials/folder_card.html
@@ -31,7 +31,7 @@
         <div class="flex justify-between items-center mb-2">
             <div class="flex space-x-1">
                 <span class="badge badge-outline">{{ folder.total_count }} emails</span>
-                <span class="badge badge-secondary">{{ folder.pending_count }} pending</span>
+                <span class="badge badge-secondary" x-tooltip.raw="{% if folder.recent_emails %}<table class='text-xs'><tr><th class='text-left pr-2'>Subject</th><th class='text-left'>Date</th></tr>{% for email in folder.recent_emails %}<tr><td class='text-left pr-2 truncate max-w-[150px]'>{{ email.subject }}</td><td class='text-left'>{{ email.date[:10] if email.date else 'N/A' }}</td></tr>{% endfor %}</table>{% else %}No recent emails{% endif %}">{{ folder.pending_count }} pending</span>
             </div>
             {% if folder.priority == 1 %}
                 <span class="badge badge-error">High Priority</span>
diff --git a/docs/design/imap-connectivity.md b/docs/design/imap-connectivity.md
index ed78f66..7e763a6 100644
--- a/docs/design/imap-connectivity.md
+++ b/docs/design/imap-connectivity.md
@@ -80,6 +80,17 @@ class User(Base, UserMixin):
     # ... existing fields ...
 ```
 
+### Folder Model Updates
+
+The `Folder` model now includes a new field for storing recent email information:
+
+```python
+class Folder(Base):
+    # ... existing fields ...
+    recent_emails = db.Column(db.JSON, default=list)  # Store recent email subjects with dates
+    # ... existing fields ...
+```
+
 ### IMAP Configuration Structure
 
 ```json
@@ -267,6 +278,83 @@ class IMAPService:
         except Exception as e:
             db.session.rollback()
             return False, f"Sync error: {str(e)}"
+    
+    def get_recent_emails(self, folder_name: str, limit: int = 3) -> List[Dict[str, any]]:
+        """Get the most recent email subjects and dates from a specific folder."""
+        try:
+            # Connect to IMAP server
+            self._connect()
+            
+            # Login
+            self.connection.login(
+                self.config.get('username', ''),
+                self.config.get('password', '')
+            )
+            
+            # Select the folder
+            resp_code, content = self.connection.select(folder_name)
+            if resp_code != 'OK':
+                return []
+            
+            # Get email IDs (most recent first)
+            resp_code, content = self.connection.search(None, 'ALL')
+            if resp_code != 'OK':
+                return []
+            
+            # Get the most recent emails (limit to 3)
+            email_ids = content[0].split()
+            recent_email_ids = email_ids[:limit] if len(email_ids) >= limit else email_ids
+            
+            recent_emails = []
+            for email_id in reversed(recent_email_ids):  # Process from newest to oldest
+                # Fetch the email headers
+                resp_code, content = self.connection.fetch(email_id, '(RFC822.HEADER)')
+                if resp_code != 'OK':
+                    continue
+                
+                # Parse the email headers
+                raw_email = content[0][1]
+                import email
+                msg = email.message_from_bytes(raw_email)
+                
+                # Extract subject and date
+                subject = msg.get('Subject', 'No Subject')
+                date_str = msg.get('Date', '')
+                
+                # Decode the subject if needed
+                try:
+                    decoded_parts = decode_header(subject)
+                    subject = ''.join([str(part, encoding or 'utf-8') if isinstance(part, bytes) else part for part, encoding in decoded_parts])
+                except Exception:
+                    pass  # If decoding fails, use the original subject
+                
+                # Parse date if available
+                try:
+                    email_date = parsedate_to_datetime(date_str) if date_str else None
+                except Exception:
+                    email_date = None
+                
+                recent_emails.append({
+                    'subject': subject,
+                    'date': email_date.isoformat() if email_date else None
+                })
+            
+            # Close folder and logout
+            self.connection.close()
+            self.connection.logout()
+            self.connection = None
+            
+            return recent_emails
+            
+        except Exception as e:
+            logging.error(f"Error getting recent emails for folder {folder_name}: {str(e)}")
+            if self.connection:
+                try:
+                    self.connection.logout()
+                except:
+                    pass
+            self.connection = None
+            return []
 ```
 
 ## Routes Implementation
diff --git a/migrations/versions/9a88c7e94083_add_recent_emails_field_to_folders_table.py b/migrations/versions/9a88c7e94083_add_recent_emails_field_to_folders_table.py
new file mode 100644
index 0000000..8c671f7
--- /dev/null
+++ b/migrations/versions/9a88c7e94083_add_recent_emails_field_to_folders_table.py
@@ -0,0 +1,32 @@
+"""Add recent_emails field to folders table
+
+Revision ID: 9a88c7e94083
+Revises: a3ad1b9a0e5f
+Create Date: 2025-08-05 11:20:32.637203
+
+"""
+from alembic import op
+import sqlalchemy as sa
+
+
+# revision identifiers, used by Alembic.
+revision = '9a88c7e94083'
+down_revision = 'a3ad1b9a0e5f'
+branch_labels = None
+depends_on = None
+
+
+def upgrade():
+    # ### commands auto generated by Alembic - please adjust! ###
+    with op.batch_alter_table('folders', schema=None) as batch_op:
+        batch_op.add_column(sa.Column('recent_emails', sa.JSON(), nullable=True))
+
+    # ### end Alembic commands ###
+
+
+def downgrade():
+    # ### commands auto generated by Alembic - please adjust! ###
+    with op.batch_alter_table('folders', schema=None) as batch_op:
+        batch_op.drop_column('recent_emails')
+
+    # ### end Alembic commands ###