diff --git a/api/calendar_manager.py b/api/calendar_manager.py
index c21deac..b0e1659 100644
--- a/api/calendar_manager.py
+++ b/api/calendar_manager.py
@@ -10,6 +10,7 @@ import subprocess
 import logging
 from datetime import datetime
 from typing import Dict, List, Optional, Any
+import bcrypt
 from base_service_manager import BaseServiceManager
 
 logger = logging.getLogger(__name__)
@@ -280,12 +281,51 @@ class CalendarManager(BaseServiceManager):
             user_dir = os.path.join(self.calendar_data_dir, 'users', username)
             self.safe_makedirs(user_dir)
 
+            # Write bcrypt entry to Radicale htpasswd (non-fatal if service not installed)
+            self._write_radicale_htpasswd(username, password)
+
             logger.info(f"Created calendar user: {username}")
             return True
         except Exception as e:
             logger.error(f"Failed to create calendar user {username}: {e}")
             return False
 
+    def _radicale_htpasswd_path(self) -> str:
+        return os.path.join(self.data_dir, 'services', 'calendar', 'config', 'users')
+
+    def _write_radicale_htpasswd(self, username: str, password: str) -> None:
+        htpasswd = self._radicale_htpasswd_path()
+        config_dir = os.path.dirname(htpasswd)
+        if not os.path.isdir(config_dir):
+            return
+        try:
+            raw = bcrypt.hashpw(password.encode('utf-8'), bcrypt.gensalt()).decode('utf-8')
+            if raw.startswith('$2b$'):
+                raw = '$2y$' + raw[4:]
+            lines = []
+            if os.path.exists(htpasswd):
+                with open(htpasswd) as f:
+                    lines = f.readlines()
+            lines = [l for l in lines if not l.startswith(f'{username}:')]
+            lines.append(f'{username}:{raw}\n')
+            with open(htpasswd, 'w') as f:
+                f.writelines(lines)
+        except Exception as e:
+            logger.warning('Failed to write Radicale htpasswd for %s: %s', username, e)
+
+    def _remove_radicale_htpasswd(self, username: str) -> None:
+        htpasswd = self._radicale_htpasswd_path()
+        if not os.path.exists(htpasswd):
+            return
+        try:
+            with open(htpasswd) as f:
+                lines = f.readlines()
+            lines = [l for l in lines if not l.startswith(f'{username}:')]
+            with open(htpasswd, 'w') as f:
+                f.writelines(lines)
+        except Exception as e:
+            logger.warning('Failed to remove Radicale htpasswd for %s: %s', username, e)
+
     def delete_calendar_user(self, username: str) -> bool:
         """Delete a calendar user"""
         try:
@@ -306,6 +346,7 @@ class CalendarManager(BaseServiceManager):
                         import shutil
                         shutil.rmtree(user_dir)
 
+                    self._remove_radicale_htpasswd(username)
                     logger.info(f"Deleted calendar user: {username}")
                     return True
             
diff --git a/api/email_manager.py b/api/email_manager.py
index 9f63cb9..7327217 100644
--- a/api/email_manager.py
+++ b/api/email_manager.py
@@ -340,12 +340,39 @@ class EmailManager(BaseServiceManager):
             mailbox_dir = os.path.join(self.email_data_dir, 'mailboxes', f'{username}@{domain}')
             self.safe_makedirs(mailbox_dir)
 
+            # Provision account in docker-mailserver (non-fatal if container not running)
+            self._dms_add_account(username, domain, password)
+
             logger.info(f"Created email user: {username}@{domain}")
             return True
         except Exception as e:
             logger.error(f"Failed to create email user {username}@{domain}: {e}")
             return False
 
+    def _dms_add_account(self, username: str, domain: str, password: str) -> None:
+        try:
+            r = subprocess.run(
+                ['docker', 'exec', 'cell-mail', 'setup', 'email', 'add',
+                 f'{username}@{domain}', password],
+                capture_output=True, text=True, timeout=30, check=False,
+            )
+            if r.returncode != 0:
+                logger.warning('dms add account %s@%s: %s', username, domain, r.stderr.strip())
+        except Exception as e:
+            logger.warning('dms add account %s@%s failed (non-fatal): %s', username, domain, e)
+
+    def _dms_del_account(self, username: str, domain: str) -> None:
+        try:
+            r = subprocess.run(
+                ['docker', 'exec', 'cell-mail', 'setup', 'email', 'del',
+                 f'{username}@{domain}'],
+                capture_output=True, text=True, timeout=30, check=False,
+            )
+            if r.returncode != 0:
+                logger.warning('dms del account %s@%s: %s', username, domain, r.stderr.strip())
+        except Exception as e:
+            logger.warning('dms del account %s@%s failed (non-fatal): %s', username, domain, e)
+
     def delete_email_user(self, username: str, domain: str) -> bool:
         """Delete an email user"""
         try:
@@ -366,6 +393,7 @@ class EmailManager(BaseServiceManager):
                         import shutil
                         shutil.rmtree(mailbox_dir)
 
+                    self._dms_del_account(username, domain)
                     logger.info(f"Deleted email user: {username}@{domain}")
                     return True
             
diff --git a/api/service_composer.py b/api/service_composer.py
index 1e0fb3f..a982d79 100644
--- a/api/service_composer.py
+++ b/api/service_composer.py
@@ -253,9 +253,21 @@ class ServiceComposer:
 
     def install(self, service_id: str, manifest: Dict,
                 template_content: str) -> Dict:
-        """Write compose file and start containers."""
+        """Write compose file, pull image, then start containers.
+
+        pull is run first so the up step doesn't time out on slow connections.
+        A single retry handles transient registry hiccups on first install.
+        """
         self.write_compose(service_id, manifest, template_content)
-        return self.up(service_id)
+        pull = self._store_cmd(service_id, 'pull', timeout=600)
+        if not pull.get('ok'):
+            logger.warning('service_composer: image pull for %s failed, proceeding anyway: %s',
+                           service_id, pull.get('stderr', '')[:200])
+        result = self.up(service_id)
+        if not result.get('ok'):
+            logger.info('service_composer: retrying up for %s after initial failure', service_id)
+            result = self.up(service_id)
+        return result
 
     def remove(self, service_id: str, purge_data: bool = False) -> Dict:
         """Stop containers, optionally delete compose file, secrets, and service data dir."""