Tiny Deathstars of Foulness

macOS Server has long had a VPN service to allow client computers to connect to a network even when they’re out of the office. The server was once capable of running the two most commonly used VPN protocols: PPTP and L2TP. And while PPTP is still accessible via the command line, L2TP is now configured by default when you setup the server using the Server app.

Setting Up The VPN Service In OS X Server

To setup the VPN service, open the Server app and click on VPN in the Server app sidebar. The VPN Settings  screen has a number of options available, as seen here.


The VPN Host Name field is used by administrators leveraging profiles. The setting used becomes the address for the VPN service in the Everyone profile. L2TP requires a shared secret or an SSL certificate. In this example, we’ll configure a shared secret by providing a password in the Shared Secret field. Additionally, there are three fields, each with an Edit button that allows for configuration:

  • Client Addresses: The dynamic pool of addresses provided when clients connect to the VPN.


  • DNS Settings: The name servers used once a VPN client has connected to the server. As well as the Search Domains configuration.


  • Routes: Select which interface (VPN or default interface of the client system) that a client connects to each IP address and subnet mask over.


  • Save Configuration Profile: Use this button to export configuration profiles to a file, which can then be distributed to client systems (macOS using the profiles command, iOS using Apple Configurator or both using Profile Manager).
  • Shared Secret: A passphrase that must be supplied by the client prior to getting a username and password prompt.

Once configured, open incoming ports on the router/firewall. While deprecated(ish) PPTP runs over port 1723. L2TP is a bit more complicated, running over 1701, but also the IP-ESP protocol (IP Protocol 50). Both are configured automatically when using Apple AirPorts as gateway devices. Officially, the ports to forward are listed at

Using The Command Line

I know, I’ve described ways to manage these services from the command line before. The serveradmin command can be used to manage the service as well as the Server app. The serveradmin command can start the service, using the default settings, with no further configuration being required:

sudo serveradmin start vpn

And to stop the service:

sudo serveradmin stop vpn

And to list the available options:

sudo serveradmin settings vpn

The output of which shows all of the VPN settings available via serveradmin (which is many more than what you see in the Server app:

vpn:vpnHost = "" = "/var/log/ppp/vpnd.log" = 1 = 128 = "jamfsw.corp" = "" = "" = "" = "1" = "" = "2" = "" = "vpn/" = no = "PPTP" = "PPP" = 5 = 1 = "EAP-RSA" = "DSACL" = 1 = 0 = 1 = 1 = 60 = 1 = "MSCHAP2" = 0 = "DSAuth" = "/var/log/ppp/vpnd.log" = 1 = 7200 = "MPPE" = _empty_array = "" = "" = _empty_array = _empty_array = "Manual" = "" = 128 = 0 = "/var/log/ppp/vpnd.log" = 1 = "jamfsw.corp" = "" = "" = "" = "1" = "" = "2" = "" = "vpn/" = yes = "L2TP" = "PPP" = 5 = 1 = "EAP-KRB" = "DSACL" = 1 = 0 = 1 = 60 = 1 = "MSCHAP2" = "DSAuth" = "/var/log/ppp/vpnd.log" = 7200 = "Keychain" = "" = "" = "SharedSecret" = "" = "None" = <> = _empty_array = "" = "" = _empty_array = _empty_array = "Manual" = "IPSec" = "Yq!XdGsVyAY?o;9jnj[X"

To disable L2TP, set to no:

sudo serveradmin settings = no

To configure how long a client can be idle prior to being disconnected:

sudo serveradmin settings = 10

By default, each protocol has a maximum of 128 sessions, configureable using

sudo serveradmin settings = 200

To see the state of the service, the pid, the time the service was configured, the path to the log files, the number of clients and other information, use the fullstatus option:

sudo serveradmin fullstatus vpn

Which returns output similar to the following:

vpn:servicePortsAreRestricted = "NO"
vpn:readWriteSettingsVersion = 1 = "MSCHAP2" = 0 = yes = "MPPEKeySize128" = "PPP" = "PPTP" = "DSAuth" = "MSCHAP2" = "PPP" = yes = 0 = "L2TP" = "DSAuth"
vpn:servicePortsRestrictionInfo = _empty_array
vpn:health = _empty_dictionary
vpn:logPaths:vpnLog = "/var/log/ppp/vpnd.log"
vpn:configured = yes
vpn:state = "STOPPED"
vpn:setStateVersion = 1

Security folk will be stoked to see that the shared secret is shown in the clear using:

Configuring Users For VPN Access

Each account that accesses the VPN server needs a valid account to do so. To configure existing users to use the service, click on Users in the Server app sidebar.


At the list of users, click on a user and then click on the cog wheel icon, selecting Edit Access to Services.


At the Service Access screen will be a list of services that could be hosted on the server; verify the checkbox for VPN is highlighted for the user. If not, click Manage Service Access, click Manage and then check the VPN box.


Setting Up Client Computers

As you can see, configuring the VPN service in macOS Server 5.2 (running on Sierra) is a simple and straight-forward process – much easier than eating your cereal with a fork and doing your homework in the dark.. Configuring clients is as simple as importing the profile generated by the service. However, you can also configure clients manually. To do so on a Mac, open the Network System Preference pane. From here, click on the plus sign (“+”) to add a new network service.


At the prompt, select VPN in the Interface field and then either PPTP or L2TP over IPSec in the VPN Type. Then provide a name for the connection in the Service Name field and click on Create.


At the list of network interfaces in the Network System Preference pane, provide the hostname or address of the server in the Server Address field and the username that will be connecting to the VPN service in the Account Name field. If using L2TP, click on Authentication Settings.


At the prompt, provide the password entered into the Shared Secret field earlier in this article in the Machine Authentication Shared Secret field and the user’s password in the User Authentication Password field. When you’re done, click OK and then provided you’re outside the network and routeable to the server, click on Connect to test the connection.


Setting Up the VPN service in macOS Server 5.2 is as simple as clicking the ON button. But much more information about using a VPN can be required. The natd binary is still built into OS X at /usr/sbin/natd and can be managed in a number of ways. And if you’re using an Apple AirPort as a router (hopefully in a very small environment) then the whole process of setting this thing up should be super-simple.

October 16th, 2016

Posted In: Mac OS X, Mac OS X Server, Mac Security

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The Time Machine service in macOS Server 5.2 hasn’t changed much from the service in previous operating systems. To enable the Time Machine service, open the Server app, click on Time Machine in the SERVICES sidebar. If the service hasn’t been enabled to date, the ON/OFF switch will be in the OFF position and no “Backup destination” will be shown in the Settings pane.


Click on the ON button to see the New Destination screen, used to configure a list of volumes as a destinations for Time Machine backups. The selection volume should be large enough to have space for all of the users that can potentially use the Time Machine service hosted on the server. When you click the Choose button, a list of volumes appears in a standard Finder selection screen.


Here, click on the volume to save your backups to in the sidebar. In most cases the Backup destination will be a mass storage device and not the boot volume of the computer. Once selected, click Choose and then if desired, limit the amount of storage on the volume to be used for backups. Click Create and a share called Backups is created and the service will start. Don’t touch anything until the service starts. Once started, add a backup destination at any time using the plus sign button (“+”) and defining another destination.


Time Machine Server works via Bonjour. Open the Time Machine System Preference pane and then click on the Select Backup Disk button from a client to see the server in the list of available targets, much as you would do with an Apple Time Capsule.


Under the hood, a backup share is creating in the file sharing service. To see the attributes of this share, use the serveradmin command followed by the settings option and then the sharing:sharePointList:_array_id:, so for a path of /Volumes/New Volume 1/Shared Items/Backups use:

sudo serveradmin settings sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups

The output indicates the options configured for the share, including how locking is handled, guest access disabled, generated identifiers and the protocols the backups share listens as:

sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:name = "Backups"
sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:smbName = "Backups"
sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:nfsExportRecord = _empty_array
sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:afpIsGuestAccessEnabled = no
sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:isTimeMachineBackup = yes
sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:dsAttrTypeNative\:sharepoint_group_id = "F4610C2C-70CD-47CF-A75B-3BAFB26D9EF3"
sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:isIndexingEnabled = yes
sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:mountedOnPath = "/Volumes/New Volume 1"
sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:dsAttrTypeStandard\:GeneratedUID = "FAB13586-2A2A-4DB2-97C7-FDD2D747A0CD"
sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:path = "/Volumes/New Volume 1/Shared Items/Backups"
sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:smbIsShared = no
sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:smbIsGuestAccessEnabled = no
sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:afpName = "Backups"
sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:smbDirectoryMask = "755"
sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:afpIsShared = yes
sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:smbCreateMask = "644"
sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:ftpName = "Backups"
sharing:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:timeMachineBackupUUID = "844A1C43-61C9-4F99-91DE-C105EA95BD45"

Once the service is running, administrators frequently fill up the target volume. To move data to another location, first stop the service and then move the folder (e.g. using mv). Once moved, use the serveradmin command to send settings to the new backup path. For example, to change the target to /Volumes/bighonkindisk, use the following command:

sudo serveradmin settings sharing:sharePointList:_array_id:/Shared Items/Backups:path = "/Volumes/bighonkindisk"

Another way to see the share and attributes of the share is through the sharing command:

sharing -l

Which should show output similar to the following:

List of Share Points
name: Backups
path: /Shared Items/Backups
afp: {
name: Backups
shared: 1
guest access: 0
inherit perms: 0
ftp: {
name: Backups
shared: 0
guest access: 0
smb: {
name: Backups
shared: 0
guest access: 0

There’s also a Bonjour service published that announces to other clients on the same subnet that the server can be used as a backup destination (the same technology used in a Time Capsule). One major update from back in Mavericks Server is the addition of the timemachine service in the severadmin command line interface. To see the command line settings for Time Machine:

sudo serveradmin settings timemachine

The output shows that share info is displayed as with the sharing service, but you can also see the GUID assigned to each share that is a part of the backup pool of storage:

timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:dsAttrTypeStandard\:GeneratedUID = "FAB13586-2A2A-4DB2-97C7-FDD2D747A0CD"
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:smbName = "Backups"
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:afpIsGuestAccessEnabled = no
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:smbDirectoryMask = "755"
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:afpName = "Backups"
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:smbCreateMask = "644"
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:nfsExportRecord = _empty_array
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:path = "/Volumes/New Volume 1/Shared Items/Backups"
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:smbIsGuestAccessEnabled = no
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:name = "Backups"
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:ftpName = "Backups"
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:smbIsShared = no
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:afpIsShared = yes
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:timeMachineBackupUUID = "844A1C43-61C9-4F99-91DE-C105EA95BD45"
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:isTimeMachineBackup = yes
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:backupQuota = 0
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:dsAttrTypeNative\:sharepoint_group_id = "F4610C2C-70CD-47CF-A75B-3BAFB26D9EF3"
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:isIndexingEnabled = yes
timemachine:sharePointList:_array_id:/Volumes/New Volume 1/Shared Items/Backups:mountedOnPath = "/Volumes/New Volume 1"
Additionally you can also query for the service to verify it’s running using full status:
sudo serveradmin fullstatus timemachine
Which outputs something similar to the following:
timemachine:command = "getState"
timemachine:state = "RUNNING"

While I found plenty to ramble on about in this article, Mass deployment is still the same, as is client side configuration.

October 15th, 2016

Posted In: Mac OS X, Mac OS X Server, Time Machine

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Every Mac by default has an application called Contacts. macOS Server 5.2, running on Sierra, has a service called Contacts. While the names might imply very different things that they do, you’ll be super-surprised that the two are designed to work with one another. The Contacts service is based on CardDAV, a protocol for storing contact information on the web, retrievable and digestible by client computers. However, there is a layer of database-driven obfuscation between the Contacts service and CardDAV. The Contacts service is also a conduit with which to read information from LDAP and display that information in the Contacts client, which is in a way similar to how the Global Address List (GAL) works in Microsoft Exchange.

I know I’ve said this about other services in macOS Server, but the Contacts service couldn’t be easier to configure. First, you should be running Open Directory and you should also have configured Apple Push Notifications. To setup Push Notifications, have an Apple ID handy and click on the Contacts entry in the SERVICES section of Server app.


Click the Edit Notifications button to configure the Apple Push Notification settings for the computer. When prompted, click on Enable Notifications.


If prompted, provide the username and password for the Apple ID and then click on Finish.
To enable the Contacts service, open the Server app and then click on Contacts in the SERVICES section of the List Pane. From here, use the “Include directory contacts in search” checkbox to publish LDAP contacts through the service, or leave this option unchecked and click on the ON button to enable the service.


The Contacts service then starts and once complete, a green light appears beside the Contacts entry in the List Pane. To configure a client open the Contacts application on a client computer and use the Preferences entry in the Contacts menu to bring up the Preferences screen. From here, click the Accounts menu and then click on Add Accounts.


At the Add Account screen, scroll down and click Add Other Account… to bring up an expanded menu of account types.


Click “CardDAV account”.


At the “Add a Contacts Account” screen, enter the email address and password of the user. Auto discovery doesn’t always work, so you might end up using the manual button to add the account using the server’s address. Alternatively, if you’ve mapped CardDAV to custom ports, you may use the advanced option to have paths and ports available.

Screen Shot 2015-09-10 at 8.24.03 AM

When the account is finished creating, you can click on the account again to see the settings used. Otherwise, close the Preferences/Accounts screen and then view the list of Contacts. Click on View and then Show Groups. This will show you the name of the servers that you’re connected to in the sidebar. There won’t be any contacts yet, so click on the plus sign to verify you have write access to the server.

Screen Shot 2015-09-10 at 8.27.44 AM
Next, let’s get access to the LDAP-based contacts. To do so, bring up the Add Account screen again and this time select LDAP Account from the Account Type field.


Provide the name or IP address of the server and then the port that LDAP contacts are available over (the defaults, 389 and 636 with SSL are more than likely the settings that you’ll use. Then click on the Continue button.

At the Account Settings screen, provide the name that will appear in the Contacts app for the account in the Description field and then enter the search base in the Search base field. To determine the search base, use the serveradmin command. The following command will output the search base:

sudo /Applications/ settings dirserv:LDAPSettings:LDAPSearchBase

Then set Authentication to simple and provide the username and password to access the server for the account you are configuring. The list then appears.

The default port for the Contacts service is 8443, as seen earlier in the configuration of the client. To customize the port, use the serveradmin command to set addressbook settings for BindSSLPorts to edit the initial array entry, as follows:

sudo /Applications/ settings addressbook:SSLPort = 8443

The default location for the files used by the Contacts service is in the /Library/Server/Calendar and Contacts directory. To change that to a folder called /Volumes/Pegasys/CardDAV, use the following command:

sudo /Applications/ settings addressbook:ServerRoot = "/Volumes/Pegasys/CardDAV"

When changing the ServerRoot, you’ll likely need to change the DataRoot, which is usually the Data directory immediately underneath the ServerRoot. To do so, run serveradmin and put the DataRoot entry under the addressbook settings:

sudo /Applications/ settings addressbook:DataRoot = "/Volumes/Pegasys/CardDAV/Data"

The service is then stopped with the serveradmin command:

sudo /Applications/ stop addressbook

And started with the serveradmin command:

sudo /Applications/ start addressbook

And whether the service is running, along with the paths to the logs can be obtained using the fullstatus command with serveradmin:

sudo /Applications/ fullstatus addressbook

The output of which should be as follows:

status addressbook
addressbook:state = “RUNNING”
addressbook:setStateVersion = 1
addressbook:readWriteSettingsVersion = 1

If you’re easily amused, run the serveradmin settings for calendar and compare them to the serveradmin settings for addressbook:

sudo /Applications/ settings calendar

By default, the Contacts server allows basic authentication. We’ll just turn that off real quick:

sudo /Applications/ settings addressbook:Authentication:Basic:Enabled = no

And then let’s see what it is in addressbook:

/Applications/ settings addressbook:Authentication:Basic:Enabled

October 12th, 2016

Posted In: Mac OS X, Mac OS X Server

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Mail is one of the hardest services to manage. Actually, mail is pretty simple in and of itself: there’s protocols people use to access their mail (such as IMAP and POP), protocols used to communicate between mail servers and send mail (SMTP, SMTPS) and then there’s a database of mail and user information. In macOS Server 5.2 for Sierra, all of these are represented by a single ON button, so it really couldn’t be easier. But then there’s the ecoysystem and the evil spammers.

As the former systems administrator of a large number of mail servers, I firmly believe that there is a special kind of hell where only spam is served at every meal for spammers. Here, the evil spammers must also read every piece of spam ever sent for eternity. By the end (aka Ragnarok), they should have the chemically induced stamina of a 16 year old with the latest Sports Illustrated Swimsuit issue, enough pills of other types to not be able to use that stamina, plenty of African princes looking to donate large sums of money if only they can be helped out of their country (which should cost about 100,000 compared to a 5,000,000 payout, not a bad ROI, right?!?!?), have their conflicting stamina situation at the top of the search engines and of course, have lost all of the money made from their African princes due to getting their credit card hijacked by about 9,000 phishing scams. All in all, a special kind of hell…

But back to the point of the article, setting up mail. The things that mail administrators need to focus on to keep that mail server flowing mail to and from everyone else in the world:

  • Static IP address. The WAN (and LAN probably) address should be static.
  • Port Forwards. Port forwards need to be configured on the gateway for the SMTP port at a minimum and more than likely other ports used to access mail on client devices (25, 143, etc)
  • DNS records. An MX record and some kind of type of record should definitely be configured for the DNS servers that are authoritative for the domain. There should also be reverse records for the address of the server, usually created by the Internet Services Provider, or ISP, that match that record.
  • Check the RBLs. If you have a new IP address you’ll be putting a DNS server on, check all the major Realtime BlackLists to make sure that some evil spammer hasn’t squatted on the IP before you got to it. This is true whether you’re in a colo, hosted on an IP you own or moving into space formerly occupied by a very standup company. A lot of IP addresses are blocked, as are blocks of IPs, so before moving mail to an IP, check it.
  • Mail filtration (message hygiene). OS X Server has a number of mail filters built in, including clam for viruses, the ability to leverage RBLs, block specific addresses and of course RBL checking. However, this is often not enough. Third party services such as MXLogic help to keep mail from coming into your network. You also end up with an external IP to send mail that can cache mail in the event the server is down and keep mail off your network in the event that it’s spam.
  • Backup. I am firmly of the belief that I’d rather not have data than not have that data backed up…

Once all of that is taken care of (I’ll add more as I think about it) then it’s time to enable the mail service in the Server app running on Yosemite. Actually, first let’s setup our SSL certificates. To do so, open the Server app and click on Certificates in the SERVER section of the sidebar. Here, use the “Secure services using” drop-down list and click on Custom… for each protocol to select the appropriate certificate to be used for the service.


Click OK when they’re all configure. Now let’s enable the mail service (or outsource mail). To do so, open the Server app and click on Mail in the SERVICES list in the sidebar.


At the configuration screen is a sparse number of settings:

  • Edit Permissions: Limits the IP addresses capable of connecting to the server.
  • Domains: Configures all of the domains the mail server will listen for mail for. Each account on the server has a short name and each domain name will be available for each short name. For example, an account with a shortname of charles will be available for email addresses of and per the Domain Name listing below.screen-shot-2016-09-26-at-9-35-20-pm
  • Authentication: Click Edit for a list of sources that accounts can authenticate against (e.g. Active Directory, Open Directory, Custom, Local, etc) and in some cases the specific password algorithms used for mail.screen-shot-2016-09-26-at-9-35-49-pm
  • Push Notifications: If Push is configured previously there’s no need to use this option. Otherwise, use your institutional APNS account to configure Push Notifications.screen-shot-2016-09-26-at-9-36-13-pm
  • Relay outgoing mail through ISP: Provide a server that all mail will get routed through from the server. For example, this might be an account with your Internet Services Provider (ISP), an account on an appliance that you own (such as a Barracuda) or with an external filtering service (such as MXLogic).screen-shot-2016-09-26-at-9-36-45-pm
  • Mailbox size: Configure the total amount of mail a user can have in the mail store, in Megabytes.
  • Edit Filtering Settings: Configure antivirus, spam assassin and junk mail filters. The “Enable virus filtering” checkbox enables clam. The “Enable blacklist filtering” checks the RBL (or RBLs) of your choice to check whether a given server is a “known” spammer and the “Enable junk mail filtering” option enables spam assassin on the host, configuring it to block based on a score as selected using the slider.

Once you’ve configured the settings for the Mail service, click on the ON slider to enable the service. At this point, you should be able to telnet into port 25 of the host to verify that SMTP is listening, preferably from another mail server:

telnet 25

You can also check that the mail services are running using the serveradmin command along with the fullstatus option for the mail service:

sudo serveradmin fullstatus mail

Which returns with some pretty verbose information about the service, including state, connections, running protocols and the rest of the following:

mail:startedTime = ""
mail:setStateVersion = 1
mail:state = "STOPPED"
mail:protocolsArray:_array_index:0:status = "ON"
mail:protocolsArray:_array_index:0:kind = "INCOMING"
mail:protocolsArray:_array_index:0:protocol = "IMAP"
mail:protocolsArray:_array_index:0:state = "STOPPED"
mail:protocolsArray:_array_index:0:service = "MailAccess"
mail:protocolsArray:_array_index:0:error = ""
mail:protocolsArray:_array_index:1:status = "ON"
mail:protocolsArray:_array_index:1:kind = "INCOMING"
mail:protocolsArray:_array_index:1:protocol = "POP3"
mail:protocolsArray:_array_index:1:state = "STOPPED"
mail:protocolsArray:_array_index:1:service = "MailAccess"
mail:protocolsArray:_array_index:1:error = ""
mail:protocolsArray:_array_index:2:status = "ON"
mail:protocolsArray:_array_index:2:kind = "INCOMING"
mail:protocolsArray:_array_index:2:protocol = "SMTP"
mail:protocolsArray:_array_index:2:state = "STOPPED"
mail:protocolsArray:_array_index:2:service = "MailTransferAgent"
mail:protocolsArray:_array_index:2:error = ""
mail:protocolsArray:_array_index:3:status = "ON"
mail:protocolsArray:_array_index:3:kind = "OUTGOING"
mail:protocolsArray:_array_index:3:protocol = "SMTP"
mail:protocolsArray:_array_index:3:state = "STOPPED"
mail:protocolsArray:_array_index:3:service = "MailTransferAgent"
mail:protocolsArray:_array_index:3:error = ""
mail:protocolsArray:_array_index:4:status = "OFF"
mail:protocolsArray:_array_index:4:kind = "INCOMING"
mail:protocolsArray:_array_index:4:protocol = ""
mail:protocolsArray:_array_index:4:state = "STOPPED"
mail:protocolsArray:_array_index:4:service = "ListServer"
mail:protocolsArray:_array_index:4:error = ""
mail:protocolsArray:_array_index:5:status = "ON"
mail:protocolsArray:_array_index:5:kind = "INCOMING"
mail:protocolsArray:_array_index:5:protocol = ""
mail:protocolsArray:_array_index:5:state = "STOPPED"
mail:protocolsArray:_array_index:5:service = "JunkMailFilter"
mail:protocolsArray:_array_index:5:error = ""
mail:protocolsArray:_array_index:6:status = "ON"
mail:protocolsArray:_array_index:6:kind = "INCOMING"
mail:protocolsArray:_array_index:6:protocol = ""
mail:protocolsArray:_array_index:6:state = "STOPPED"
mail:protocolsArray:_array_index:6:service = "VirusScanner"
mail:protocolsArray:_array_index:6:error = ""
mail:protocolsArray:_array_index:7:status = "ON"
mail:protocolsArray:_array_index:7:kind = "INCOMING"
mail:protocolsArray:_array_index:7:protocol = ""
mail:protocolsArray:_array_index:7:state = "STOPPED"
mail:protocolsArray:_array_index:7:service = "VirusDatabaseUpdater"
mail:protocolsArray:_array_index:7:error = ""
mail:logPaths:Server Error Log = "/Library/Logs/Mail/mail-err.log"
mail:logPaths:IMAP Log = "/Library/Logs/Mail/mail-info.log"
mail:logPaths:Server Log = "/Library/Logs/Mail/mail-info.log"
mail:logPaths:POP Log = "/Library/Logs/Mail/mail-info.log"
mail:logPaths:SMTP Log = "/var/log/mail.log"
mail:logPaths:List Server Log = "/Library/Logs/Mail/listserver.log"
mail:logPaths:Migration Log = "/Library/Logs/MailMigration.log"
mail:logPaths:Virus Log = "/Library/Logs/Mail/clamav.log"
mail:logPaths:Amavisd Log = "/Library/Logs/Mail/amavis.log"
mail:logPaths:Virus DB Log = "/Library/Logs/Mail/freshclam.log"
mail:imapStartedTime = ""
mail:postfixStartedTime = ""
mail:servicePortsRestrictionInfo = _empty_array
mail:servicePortsAreRestricted = "NO"
mail:connectionCount = 0
mail:readWriteSettingsVersion = 1
mail:serviceStatus = "DISABLED"

To stop the service:

sudo serveradmin stop mail

And to start it back up:

sudo serveradmin start mail

To configure some of the settings no longer in the GUI from previous versions, let’s look at the full list of options:

sudo serveradmin settings mail

One that is commonly changed is the subject line added to messages that are marked as spam by spam assassin. This is stored in mail:postfix:spam_subject_tag, so changing would be:

sudo serveradmin settings mail:postfix:spam_subject_tag = "***DIEEVILSPAMMERSDIE*** "

A number of admins also choose to disable greylisting, done using the mail:postfix:greylist_disable option:

sudo serveradmin settings mail:postfix:greylist_disable = no

To configure an email address for quarantined mail to go, use mail:postfix:virus_quarantine:

sudo serveradmin settings mail:postfix:virus_quarantine = ""

The administrator, by default, doesn’t get an email when an email containing a file infected with a virus is sent through the server. To enable this option:

sudo serveradmin settings mail:postfix:virus_notify_admin = yes

I also find a lot of Mac environments want to accept email of pretty much any size. By default, message size limits are enabled. To disable:

sudo serveradmin settings mail:postfix:message_size_limit_enabled = yes

Or even better, just set new limit:

sudo serveradmin settings mail:postfix:message_size_limit = 10485760

And to configure the percentage of someone’s quota that kicks an alert (soft quota):

sudo serveradmin settings mail:imap:quotawarn = 75

Additionally, the following arrays are pretty helpful, which used to have GUI options:

  • mail:postfix:mynetworks:_array_index:0 = “″ – Add entries to this one to add “local” clients
  • mail:postfix:host_whitelist = _empty_array – Add whitelisted hosts
  • mail:postfix:blacklist_from = _empty_array – Add blacklisted hosts
  • mail:postfix:black_hole_domains:_array_index:0 = “” – Add additional RBL Servers

The client side of the mail service is straight forward enough. If you are wondering where in this article we discuss using webmail, er, that’s not installed by default any longer. But the open source project previously used, roundcube, is still available for download and easily installed (the pre-reqs are all there, already). Check out the roundcube wiki installation page here for more info on that. Also, mail groups. I hope to have a post about that soon enough. Unless, of course, I get sidetracked with having a life. Which is arguably not very likely…

October 11th, 2016

Posted In: Mac OS X, Mac OS X Server, Mac Security

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The software patching configuration built into most operating systems is configured so that all a user has to do is open a box at home, join the network and start using the computer right away. As environments grow from homes to small offices and then small offices grow into enterprises, at some point software updates and patches need to be managed centrally. OS X Server 5.2 (on Sierra), as with its macOS Server predecessors has a Software Update service. The service in the Server app is known as Software Update and from the command line is known as swupdate.

The Software Update service, by default, stores each update in the /var/db/swupd directory. The Software Update service is actually comprised of three components. The first is an Apache server, invoked by the /Applications/ LaunchDaemon. This LaunchDaemon invokes a httpd process and clients access updates from the server based on a manifest of updates available in the sucatalog.

These are synchronized with Apple Software Updates via /Applications/, the LaunchDaemon for swupdate at /Applications/

Clients can be pointed at the server then via a Profile or using the defaults command to edit the /Library/Preferences/ file. The contents of this file can be read using the following command:

defaults read /Library/Preferences/

To point a client to a server via the command line, use a command such as the following:

sudo defaults write /Library/Preferences/ CatalogURL

But first, you’ll need to configure and start the Software Update service. Lucky you, it’s quick (although quick in a hurry up and wait kind of way). To get started, click on the View menu in Server and select the Software Update service.


By default, updates are set to simply mirror the Apple servers, by default, enabling each update that Apple publishes, effectively proxying updates. You can use the Manual button if you would like to configure updates to either manually be approved and manually synchronized or just manually approved but automatically copied from Apple. Otherwise click on the ON button and wait for the updates to cache to simply mirror the Apple servers. If you would like to manually configure updates, click on the Manual option and then click on the Updates tab.

The first item in the Updates tab is the “Automatically download new updates” checkbox. This option downloads all of the updates but does not enable them. The Updates tab also displays all available updates. click on one and then click on the cog-wheel icon towards the bottom of the screen to configure its behavior (Download, Enable, Disable, Remove and View Update).

Note: The only option for updates in an Automatic configuration environment is disable.

The service can be managed using serveradmin. To start Software Update, use the start option, followed by the swupdate service identifier:

sudo /Applications/ start swupdate

To stop the service, replace start with stop:

sudo /Applications/ stop swupdate

To see the status of the service, including the location of updates, the paths to log files, when the service was started and the number of updates running, use the fullstatus option:

sudo /Applications/ fullstatus swupdate

The output of which appears as follows:

swupdate:state = "RUNNING"
swupdate:lastChecktime = 2016-08-07 01:25:05 +0000
swupdate:syncStatus = "INPROGRESS"
swupdate:syncServiceState = "RUNNING"
swupdate:setStateVersion = 1
swupdate:lastProductsUpdate = 2016-08-16 04:02:16 +0000
swupdate:logPaths:swupdateAccessLog = "/var/log/swupd/swupd_access_log"
swupdate:logPaths:swupdateErrorLog = "/var/log/swupd/swupd_error_log"
swupdate:logPaths:swupdateServiceLog = "/var/log/swupd/swupd_syncd_log"
swupdate:readWriteSettingsVersion = 1
swupdate:pluginVers = "10.12"
swupdate:checkError = no
swupdate:updatesDocRoot = "/Library/Server/Software Update/Data/"
swupdate:hostServiceState = "RUNNING"
swupdate:autoMirror = no
swupdate:numOfEnabledPkg = 0
swupdate:servicePortsAreRestricted = "NO"
swupdate:numOfMirroredPkg = 0
swupdate:autoMirrorOnlyNew = no
swupdate:startTime = 2016-08-07 01:25:05 +0000
swupdate:autoEnable = no

There are also a number of options available using the serveradmin settings that aren’t exposed to the Server app. Available Settings include:

swupdate:checkError = no
swupdate:limitBandwidth = no
swupdate:PurgeUnused = yes
swupdate:portToUse = 8088
swupdate:autoEnable = yes
swupdate:valueBandwidth = 0
swupdate:syncStatus = “Initializing”
swupdate:autoMirror = yes
swupdate:syncBandwidth = 0
swupdate:updatesDocRoot = “/Library/Server/Software Update/Data/”
swupdate:autoMirrorOnlyNew = no

These include a feature I used to use a lot in the beginning of deployments with poor bandwidth, only mirroring new updates, which is available to swupdate via the autoMirrorOnlyNew option. To configure:

sudo /Applications/ settings swupdate:autoMirrorOnlyNew = yes

Also, the service can throttle bandwidth for clients. To use this option, run the following command:

sudo /Applications/ settings swupdate:limitBandwidth = yes

And configure bandwidth using the syncBandwidth option, as follows:

sudo /Applications/ settings swupdate:syncBandwidth = 10

To automatically sync updates but not enable them (as the checkboxes allow for in the Server app, use the following command:

sudo /Applications/ settings swupdate:autoEnable = no

The port (by default 8088) can be managed using the portToUse option, here being used to set it to 80 (clients need this in their catalog URL from here on out):

sudo /Applications/ settings swupdate:portToUse = 80

Finally, administrators can purge old packages that are no longer needed using the PurgeUnused option:

sudo /Applications/ settings swupdate:PurgeUnused = yes

One of the biggest drawbacks of the Software Update is the fact that it does not allow for serving 3rd party packages (not that Apple has much control over this, since these aren’t sourced from the App Store) from vendors such as Microsoft or Adobe. To provide those vendors with a manifest file and a quick little path option to add those manifest files while doing a little man in the middle protection would be a nice middle ground between the Mac App Store and the built in software update options in macOS. But then, we wouldn’t want to make it too easy. I don’t know, maybe by creating the Caching service… 😉

October 10th, 2016

Posted In: Mac OS X, Mac OS X Server

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In order to use the Apple Volume Purchase Program (VPP), you will need an MDM solution (Profile Manager, Casper, MobileIron, Meraki, FileWave, etc). The same program is used for device-based VPP or user-based VPP. One change since 10.11 is that there are now two programs, which is meant to simplify the experience of setting up your MDM solution and long-term maintenance. The first is the traditional VPP account, available to companies and other non-educational environments that have a DUNS number. The second is the newer Apple School Manager, for educational institutions.

Before starting to buy apps and associating those apps from an MDM solution, there are a few things you should know. The first is that your organization can have multiple VPP tokens or Apple School Manager tokens, and you can hierarchically manage apps this way. The second is that each token should only be installed on one MDM solution or server (if you have multiple instances of the same solution). Therefore, if you’re going to have multiple servers or solutions for managing apps, keep in mind to buy apps for groups based on the VPP account that will be associated with devices for each solution.

Also, note that the traditional deployment mechanism of VPP is user, or Apple ID-based VPP apps. Here, you associate an Apple ID to a VPP account from an MDM and then the administrator sends apps to devices based via the MDM solution. And this is still an option. In 10.11 and iOS 9 we got device-based VPP. Here, you can send apps to devices even if they don’t have Apple IDs associated to the device, and you can send apps automatically, meaning they will not require user interaction. This makes VPP multi-tenant and great for school labs, or shared-use Macs and iOS devices.

But this article isn’t about the fine print details of the new VPP. Instead, this article is about making Profile Manager work with your new VPP token. Before you get started, know that when you install your vpptoken, if it’s in use by another MDM, Profile Manager will unlicensed all apps with your other MDM. To get started, log into your VPP account. Once logged in, click on your account email address and then select Account Summary.


Then, click on the Download Token link and your token will be downloaded to your ~/Downloads (or wherever you download stuff).


Once you have your token, open the Server app and click on the Profile Manager service.


Click on the checkbox for Distribute apps and books from the Volume Purchase Program.


At the VPP Managed Distribution screen, drag the .vpptoken file downloaded earlier into the screen.


Click Continue. The VPP code email address will appear in the screen. Click Done.

Back at the profile manager screen, you should then see that the checkbox is filled and you can now setup Profile Manager.

The rest of the configuration of Profile Manager is covered in a previous article.

Note: The account used to configure the VPP information is not tracked in any serveradmin settings.

October 9th, 2016

Posted In: Mac OS X, Mac OS X Server

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macOS Server 5.2, running on Sierra, comes with a few new alerting options previously unavailable in versions of OS X. The alerts are sent to administrators via servermgrd and configured in the 5th version of the Server app. To configure alerts on the server, open the Server app and then click on Alerts in the Server app sidebar. Next, click on the Delivery tab.


At the Delivery screen, click on the Edit button for Email Addresses and enter every email address that should receive alerts sent from the server. Then click on the Edit button for Push Notifications. Here, check the box for each administrator of the server. The email address on file for the user then receives push notifications of events from the server.


Click on OK when you’ve configured all of the appropriate administrators for alerting. Click on the Edit… button for Push and if Push notifications are not already enabled you will run through the Push Notification configuration wizard.


Then, check the boxes for Email and Push for each of the alerts you want to receive (you don’t have to check both for each entry). Alerts have changed in macOS Server, they are no longer based on the SMART status of drives or capacity; instead Delivery is now based on service settings.

Finally, as with previous versions of macOS Server, snmp is built in. The configuration file for which is located in the /private/etc/snmp/snmpd.conf and the built-in LaunchDaemon is, where the actual binary being called is /usr/sbin/snmpd (and by default it’s called with a -f option). Once started, the default community name should be COMMUNITY (easily changed in the conf file) and to test, use the following command from a client (the client is in the following example):

snmpwalk -On -v 1 -c COMMUNITY

October 9th, 2016

Posted In: Mac OS X, Mac OS X Server, Mac Security

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macOS Server 5.2 running on Sierra 10.12) has an adaptive firewall built in, or a firewall that controls incoming access based on clients attempting to abuse the server. The firewall automatically blocks incoming connections that it considers to be dangerous. For example, if a client attempts too many incorrect logins then a firewall rule restricts that user from attempting to communicate with the server for 15 minutes. If you’re troubleshooting and you accidentally tripped up one of these rules then it can be a bit frustrating. Which is why Apple gives us afctl, a tool that interacts with the adaptive firewall.

The most basic task you can do with the firewall is to disable all of the existing rules. To do so, simply run afctl (all afctl options require sudo) with a -d option:

/Applications/ -d

When run, the adaptive firewall’s rules are disabled. To re-enable them, use the -e option:

/Applications/ -e

Turning off the rules seems a bit much for most troubleshooting tasks. To remove a specific IP address that has been blacklisted, use the -r option followed by the IP address (rules are enforced by IP):

/Applications/ -r

To add an IP to the blacklist, use the -a option, also followed by the IP:

/Applications/ -a

To permanently add a machine to the whitelist, use -w with the IP:

/Applications/ -w

And to remove a machine, use -x. To understand what is going on under the hood, consider this. The blacklisted computers are stored in plain text in /var/db/af/blacklist and the whitelisted computers are stored in the same path in a file called whitelist. The afctl binary itself is stored in /usr/libexec/afctl and the service is enabled by /System/LIbrary/LaunchDaemons/, meaning to stop the service outright, use launchctl:

launchctl unload


The configuration file for afctl is at /etc/af.plist. Here you can change the path to the blacklist and whitelist files, change the interval with which it is run, etc. Overall, the adaptive firewall is a nice little tool for Mac OS X Server security, but also something a number of open source tools can do as well. But for something built-in and easy, worth using.

There’s a nice little command called hb_summary located in /Applications/ that provides statistics for blocked hosts. To see statistics about how much the Adaptive Firewall is being used, just run the command with no options:


The output provides the following information (helpful if plugging this information into a tool like Splunk):

  • Date
  • Date statistics start
  • Number of hosts blocked
  • Addresses blocked
  • Number of times each address was blocked
  • Last time a host was blocked
  • Total number of times a block was issued

October 8th, 2016

Posted In: Mac OS X, Mac OS X Server, Mac Security

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There are a few ways to create users in macOS Server 5.2, running on Sierra. The first is using the Server app, the second is using using the Users & Groups System Preference pane and the third is using the command line. In this article we will look at creating users in the Server app.

To do so, open the Server app and connect to your server. Then click on the Users entry in the ACCOUNTS list. The list of users is displayed, based on the directory domain(s) being browsed. A directory domain is a repository of account data, which can include local users, local network users and users in a shared directory service such as Open Directory and Active Directory.


The drop-down list allows you to see objects that are stored locally as well as on a shared directory server. Therefore, clicking All Users will show all of the accounts accessible by the system. Click on the plus sign to create a new account. At this point, if the server has been promoted to an Open Directory Master, the account will be a local network account, with no way of choosing a different location to store the account in the Server app.


When prompted, provide the following information about the new user:

  • Full Name: Usually the first and last name of the user.
  • Account Name: A shorter representation of that name with no spaces or special characters.
  • Email address: The email address to use if the account is going over quotas, has calendar invitations sent, or used for email hosted on the server, etc.
  • Password: The password the user will use to access services on the server.
  • Verify: The password a second time to make sure there are no spelling errors.
  • Allow user to administer this server: Optional field that grants the user administrative access to the server.
  • Home Folder: Optional field that by default creates local home directories for users that use the account but that also allows you to select a directory shared using the File Sharing service as a location for home folders. Each user in OS X has a home folder, this option defines whether that folder will reside on their computer or on a central server.
  • Limit Disk Usage To: Define the amount of space an account can take up on servers.
  • Keywords: Keywords, or tags, for the user.
  • Notes: Any notes you want to enter into the user record.

Note: Optionally, you can also drag an image onto the image shown in the New User screen if you’d like the user to have an avatar.

Once the account details are as you would like, click on the Done button. The account will then be displayed in the list of available accounts. Once the account is created, highlight it and click on the cog wheel icon below the list of accounts. Here, you have the option to edit the account you just created, edit their access to services hosted on the server, configure email information and change their password.


Click Edit User. Here, you have two new features. You can add the user to groups and use the checkbox for “log in” to disable the account.


Click Cancel and then using the cog wheel menu again, click on Edit Access to Services. Here, uncheck each service that the user should not have access to. If the service isn’t running then it’s not a big deal. You can highlight multiple accounts concurrently and then use this option to disable services for users en masse.

October 6th, 2016

Posted In: Mac OS X, Mac OS X Server

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There is a nifty feature available in the profiles command in Sierra (which dates back to Mavericks), where you can configure profiles to install at the next boot, rather than immediately. Useful in a number of scenarios. Use the -s to define a startup profile and take note that if it fails, the profile will attempt to install at each subsequent reboot until installed. To use the command, simply add a -s then the -F for the profile and the -f to automatically confirm, as follows (and I like to throw in a -v usually for good measure):

profiles -s -F /Profiles/SuperAwesome.mobileconfig -f -v

And that’s it. Nice and easy and you now have profiles that only activate when a computer is started up.

October 4th, 2016

Posted In: Mac OS X, Mac OS X Server

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