Fix email configuration: Update SMTP port to 587 and regenerate Gmail app password

.env

@@ -1,7 +1,7 @@
 SMTP_HOST=smtp.gmail.com
-SMTP_PORT=2525
+SMTP_PORT=587
 SMTP_SECURE=false
 RECIPIENT_EMAIL=eliza@deafgain.org
 GOOGLE_EMAIL=system@deafgain.org
-GOOGLE_APP_PASSWORD=ojvlysraxwjriwzy 
+GOOGLE_APP_PASSWORD=idjcxxwzvloorfuk
 # REDIS_URL=redis://localhost:6379

Caddyfile

@@ -0,0 +1,127 @@
+{                     
+    admin 0.0.0.0:2019
+    email chris@sigd.net
+}
+
+# Internal Services
+gitea.sigd.net {
+    reverse_proxy 10.4.0.156:3000
+} 
+
+statistics.deafgain.org {
+    reverse_proxy matomo:80
+}
+
+archives.sigd.net {
+    reverse_proxy 10.4.0.159:8001
+}
+
+upload.sigd.net {
+    reverse_proxy 10.4.0.159:4174
+}
+
+preview.sigd.net {
+    reverse_proxy 10.4.0.83:3000
+}
+
+droppy.sigd.net {
+    reverse_proxy 10.4.0.159:6969
+}
+
+upload.sigd.net/api/* {
+    # Forward API requests to the backend API service
+    uri strip_prefix /api
+    reverse_proxy 10.4.0.159:3334
+}
+
+requests.sigd.net {
+    reverse_proxy 10.4.0.157:5055
+}
+
+documents.deafgain.org {
+    reverse_proxy 10.4.0.156:8001
+}
+
+documents.sigd.net {
+    reverse_proxy 10.4.0.159:8001
+}
+
+doculens.deafgain.org {
+    reverse_proxy 10.4.0.156:5015
+}
+
+firewall.sigd.net {
+    reverse_proxy 10.4.0.1:9080
+}
+
+# Public Websites (on this VM - 10.4.0.205)
+
+# Deaf Summit Website
+deafsummit.org {
+    # Route API requests to backend
+    handle /api/* {
+        reverse_proxy localhost:808
+    }
+
+    # Route everything else to frontend
+    handle {
+        reverse_proxy localhost:807
+    }
+}
+
+www.deafsummit.org {
+    redir https://deafsummit.org{uri} permanent
+}
+
+# DeafMissoula.org
+www.deafmissoula.org {
+    redir https://deafmissoula.org{uri} permanent
+}
+
+deafmissoula.org {
+    reverse_proxy 172.18.0.7:801
+}
+
+# ChrisHaulmark.com
+www.chrishaulmark.com {
+    redir https://chrishaulmark.com{uri} permanent
+}
+
+chrishaulmark.com {
+    reverse_proxy chrishaulmark-website-web-1:803
+}
+
+# DeafGain.org
+www.deafgain.org {
+    redir https://deafgain.org{uri} permanent
+}
+
+deafgain.org {
+    reverse_proxy 172.18.0.4:804
+}
+
+# FinLion domains
+finlion.com {
+    reverse_proxy finlion-website-web-1:805
+}
+
+www.finlion.com {
+    redir https://finlion.com{uri} permanent
+}
+
+finlion.net, www.finlion.net {
+    redir https://finlion.com{uri} permanent
+}
+
+finlion.org, www.finlion.org {
+    redir https://finlion.com{uri} permanent
+}
+
+# MAD Lawsuit
+www.mad-lawsuit.org {
+    redir https://mad-lawsuit.org{uri} permanent
+}
+
+mad-lawsuit.org {
+    reverse_proxy mad-lawsuit-frontend-1:806
+}

cline_docs/activeContext.md

@@ -281,31 +281,45 @@ Successfully removed ADA-Compliant Transcripts service from the Services page pe
 - `src/pages/Services.tsx` - Removed ADA transcribing service and cleaned imports
 
 ## Recently Completed Work  
-**Date: 9/11/2025**
+**Date: 1/9/2026**
 
-### ✅ Email Configuration Updates - COMPLETED
-Successfully updated email system configuration per user request:
+### ✅ Email Configuration Fix - COMPLETED
+Successfully resolved Gmail authentication issue and updated email configuration:
+
+**Root Cause Identified:**
+- Google password was changed on January 8, 2026
+- This automatically revoked all existing app passwords for security
+- Old app password (ojvlysraxwjriwzy) was no longer valid
 
 **Changes Made:**
-- **SMTP Port Updated**: Changed Gmail SMTP port from 587 to 2525 in `.env` file
-- **Redis Temporarily Disabled**: Commented out `REDIS_URL` to disable Redis caching/rate limiting
-- **Reason**: User requested port change and temporary Redis disable for troubleshooting
+- **SMTP Port Corrected**: Changed from 2525 to 587 (standard Gmail SMTP port with STARTTLS)
+- **App Password Updated**: Generated new Gmail app password (idjcxxwzvloorfuk)
+- **Configuration Tested**: Verified with test email to chris@sigd.net
 
 **Current Email Configuration:**
 - **SMTP Host**: smtp.gmail.com
-- **SMTP Port**: 2525 (updated from 587)
-- **SMTP Secure**: false
+- **SMTP Port**: 587 (standard port with STARTTLS)
+- **SMTP Secure**: false (uses STARTTLS)
 - **Sender**: system@deafgain.org
 - **Recipient**: eliza@deafgain.org
-- **Status**: ✅ Ready for Docker rebuild with new settings
+- **App Password**: idjcxxwzvloorfuk (generated 1/9/2026)
+- **Status**: ✅ **FULLY OPERATIONAL** - Test email sent successfully
+
+**Test Results:**
+```
+✅ SMTP connection verified successfully!
+✅ Test email sent successfully!
+Message ID: <99a88457-6604-ca19-a17c-60daa7a317ae@deafgain.org>
+Response: 250 2.0.0 OK  1767992239 41be03b00d2f7-c4cc96ca7a9sm11346262a12.25 - gsmtp
+```
 
 **Rate Limiting Status:**
-- **Redis**: ⚠️ Temporarily disabled
+- **Redis**: ⚠️ Temporarily disabled (commented out in .env)
 - **Fallback**: Rate limiting code allows all requests when Redis unavailable
 - **Impact**: Contact and subscription forms will work without rate limiting protection
 
 **Files Modified:**
-- `.env` - Updated SMTP_PORT=2525, commented out REDIS_URL
+- `.env` - Updated SMTP_PORT=587, updated GOOGLE_APP_PASSWORD, Redis still commented out
 
 ## Status Summary
 🟢 **EMAIL SYSTEM UPDATED** - SMTP port changed to 2525, Redis temporarily disabled. Email functionality will work after Docker rebuild, but without rate limiting protection. Services page updated to reflect current service offerings. Interactive map successfully expanded with additional 2025 conference locations in New Orleans and Austin. Ready for production use and content addition.