diff --git a/.env.example b/.env.example
index c732b96..b6391fc 100644
--- a/.env.example
+++ b/.env.example
@@ -94,8 +94,9 @@ EMAIL_HMAC_SECRET=
 MAILGUN_SIGNATURE_VALIDATION=true
 
 # Obsidian Configuration (headless sync)
-# Auth token from Obsidian account (Settings → Account → API token)
-OBSIDIAN_AUTH_TOKEN=your-obsidian-auth-token
+# Obsidian account credentials (used for `ob login` on container startup)
+OBSIDIAN_EMAIL=your-obsidian-email
+OBSIDIAN_PASSWORD=your-obsidian-password
 # Vault ID to sync (found in Obsidian sync settings)
 OBSIDIAN_VAULT_ID=your-vault-id
 # End-to-end encryption password (if vault uses E2E encryption)
diff --git a/docker-compose.yml b/docker-compose.yml
index 0136a87..d8953a8 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -51,7 +51,8 @@ services:
       - ALLOWED_WHATSAPP_NUMBERS=${ALLOWED_WHATSAPP_NUMBERS}
       - TWILIO_SIGNATURE_VALIDATION=${TWILIO_SIGNATURE_VALIDATION:-true}
       - TWILIO_WEBHOOK_URL=${TWILIO_WEBHOOK_URL:-}
-      - OBSIDIAN_AUTH_TOKEN=${OBSIDIAN_AUTH_TOKEN}
+      - OBSIDIAN_EMAIL=${OBSIDIAN_EMAIL}
+      - OBSIDIAN_PASSWORD=${OBSIDIAN_PASSWORD}
       - OBSIDIAN_VAULT_ID=${OBSIDIAN_VAULT_ID}
       - OBSIDIAN_E2E_PASSWORD=${OBSIDIAN_E2E_PASSWORD}
       - OBSIDIAN_DEVICE_NAME=${OBSIDIAN_DEVICE_NAME}
diff --git a/startup.sh b/startup.sh
index 93702ed..50d3102 100644
--- a/startup.sh
+++ b/startup.sh
@@ -8,8 +8,25 @@ mkdir -p /app/data/obsidian
 
 # Start continuous Obsidian sync if enabled
 if [ "${OBSIDIAN_CONTINUOUS_SYNC}" = "true" ]; then
-    echo "Starting Obsidian continuous sync in background..."
-    ob sync --continuous &
+    echo "Setting up Obsidian sync..."
+
+    VAULT_PATH="${OBSIDIAN_VAULT_PATH:-/app/data/obsidian}"
+
+    # Login
+    ob login --email "${OBSIDIAN_EMAIL}" --password "${OBSIDIAN_PASSWORD}" && \
+    # Setup sync for vault
+    ob sync-setup \
+        --vault "${OBSIDIAN_VAULT_ID}" \
+        --path "${VAULT_PATH}" \
+        --password "${OBSIDIAN_E2E_PASSWORD}" \
+        --device-name "${OBSIDIAN_DEVICE_NAME:-simbarag}" && \
+    # Start continuous sync in background
+    echo "Starting Obsidian continuous sync..." && \
+    ob sync --continuous --path "${VAULT_PATH}" &
+
+    if [ $? -ne 0 ]; then
+        echo "WARNING: Obsidian sync setup failed. Continuing without sync."
+    fi
 fi
 
 echo "Starting application..."