Content-type: text/html Manpage of IPSEC_PLUTO


Section: Maintenance Commands (8)
Updated: 28 March 1999
Index Return to Main Contents


ipsec pluto - IPsec IKE keying daemon
ipsec whack - control interface for IPSEC keying daemon  


ipsec pluto [--help] [--version] [--optionsfrom filename] [--nofork] [--stderrlog] [--noklips] [--uniqueids] [--interface interfacename] [--ikeport portnumber] [--ctlbase path] [--secretsfile secrets-file] [--adns pathname] [--lwdnsq pathname] [--perpeerlog] [--perpeerlogbase dirname] [--debug-none] [--debug-all] [--debug-raw] [--debug-crypt] [--debug-parsing] [--debug-emitting] [--debug-control] [--debug-lifecycle] [--debug-klips] [--debug-dns] [--debug-oppo] [--debug-private]
ipsec whack [--help] [--version]
ipsec whack --name connection-name
[--id id] [--host ip-address] [--ikeport port-number] [--nexthop ip-address] [--client subnet] [--dnskeyondemand] [--updown updown]
[--id id] [--host ip-address] [--ikeport port-number] [--nexthop ip-address] [--client subnet] [--dnskeyondemand] [--updown updown]
[--psk] [--rsasig] [--encrypt] [--compress] [--tunnel] [--pfs] [--disablearrivalcheck] [--ipv4] [--ipv6] [--tunnelipv4] [--tunnelipv6] [--ikelifetime seconds] [--ipseclifetime seconds] [--rekeymargin seconds] [--rekeyfuzz percentage] [--keyingtries count] [--dontrekey] [--delete] [--ctlbase path] [--optionsfrom filename] [--label string]
ipsec whack --keyid id [--addkey] [--pubkeyrsa key] [--ctlbase path] [--optionsfrom filename] [--label string]
ipsec whack --myid id
ipsec whack --listen|--unlisten [--ctlbase path] [--optionsfrom filename] [--label string]
ipsec whack --route|--unroute --name connection-name [--ctlbase path] [--optionsfrom filename] [--label string]
ipsec whack --initiate|--terminate --name connection-name [--asynchronous] [--ctlbase path] [--optionsfrom filename] [--label string]
ipsec whack [--tunnelipv4] [--tunnelipv6] --oppohere ip-address --oppothere ip-address
ipsec whack --delete --name connection-name [--ctlbase path] [--optionsfrom filename] [--label string]
ipsec whack --deletestate state-number [--ctlbase path] [--optionsfrom filename] [--label string]
ipsec whack [--name connection-name] [--debug-none] [--debug-all] [--debug-raw] [--debug-crypt] [--debug-parsing] [--debug-emitting] [--debug-control] [--debug-lifecycle] [--debug-klips] [--debug-dns] [--debug-oppo] [--debug-private] [--ctlbase path] [--optionsfrom filename] [--label string]
ipsec whack --status [--ctlbase path] [--optionsfrom filename] [--label string]
ipsec whack --shutdown [--ctlbase path] [--optionsfrom filename] [--label string]


pluto is an IKE (``IPsec Key Exchange'') daemon. whack is an auxiliary program to allow requests to be made to a running pluto.

pluto is used to automatically build shared ``security associations'' on a system that has IPsec, the secure IP protocol. In other words, pluto can eliminate much of the work of manual keying. The actual secure transmission of packets is the responsibility of other parts of the system (see KLIPS, the companion implementation of IPsec). ipsec_auto(8) provides a more convenient interface to pluto and whack.  

IKE's Job

A Security Association (SA) is an agreement between two network nodes on how to process certain traffic between them. This processing involves encapsulation, authentication, encryption, or compression.

IKE can be deployed on a network node to negotiate Security Associations for that node. These IKE implementations can only negotiate with other IKE implementations, so IKE must be on each node that is to be an endpoint of an IKE-negotiated Security Association. No other nodes need to be running IKE.

An IKE instance (i.e. an IKE implementation on a particular network node) communicates with another IKE instance using UDP IP packets, so there must be a route between the nodes in each direction.

The negotiation of Security Associations requires a number of choices that involve tradeoffs between security, convenience, trust, and efficiency. These are policy issues and are normally specified to the IKE instance by the system administrator.

IKE deals with two kinds of Security Associations. The first part of a negotiation between IKE instances is to build an ISAKMP SA. An ISAKMP SA is used to protect communication between the two IKEs. IPsec SAs can then be built by the IKEs - these are used to carry protected IP traffic between the systems.

The negotiation of the ISAKMP SA is known as Phase 1. In theory, Phase 1 can be accomplished by a couple of different exchange types, but we only implement one called Main Mode (we don't implement Aggressive Mode).

Any negotiation under the protection of an ISAKMP SA, including the negotiation of IPsec SAs, is part of Phase 2. The exchange type that we use to negotiate an IPsec SA is called Quick Mode.

IKE instances must be able to authenticate each other as part of their negotiation of an ISAKMP SA. This can be done by several mechanisms described in the draft standards.

IKE negotiation can be initiated by any instance with any other. If both can find an agreeable set of characteristics for a Security Association, and both recognize each others authenticity, they can set up a Security Association. The standards do not specify what causes an IKE instance to initiate a negotiation.

In summary, an IKE instance is prepared to automate the management of Security Associations in an IPsec environment, but a number of issues are considered policy and are left in the system administrator's hands.  


pluto is an implementation of IKE. It runs as a daemon on a network node. Currently, this network node must be a LINUX system running the KLIPS implementation of IPsec.

pluto only implements a subset of IKE. This is enough for it to interoperate with other instances of pluto, and many other IKE implementations. We are working on implementing more of IKE.

The policy for acceptable characteristics for Security Associations is mostly hardwired into the code of pluto (spdb.c). Eventually this will be moved into a security policy database with reasonable expressive power and more convenience.

pluto uses shared secrets or RSA signatures to authenticate peers with whom it is negotiating.

pluto initiates negotiation of a Security Association when it is manually prodded: the program whack is run to trigger this. It will also initiate a negotiation when KLIPS traps an outbound packet for Opportunistic Encryption.

pluto implements ISAKMP SAs itself. After it has negotiated the characteristics of an IPsec SA, it directs KLIPS to implement it. It also invokes a script to adjust any firewall and issue route(8) commands to direct IP packets through KLIPS.

When pluto shuts down, it closes all Security Associations.  

Before Running Pluto

pluto runs as a daemon with userid root. Before running it, a few things must be set up.

pluto requires KLIPS, the FreeS/WAN implementation of IPsec. All of the components of KLIPS and pluto should be installed.

pluto supports multiple public networks (that is, networks that are considered insecure and thus need to have their traffic encrypted or authenticated). It discovers the public interfaces to use by looking at all interfaces that are configured (the --interface option can be used to limit the interfaces considered). It does this only when whack tells it to --listen, so the interfaces must be configured by then. Each interface with a name of the form ipsec[0-9] is taken as a KLIPS virtual public interface. Another network interface with the same IP address (there should be only one) is taken as the corresponding real public interface. ifconfig(8) with the -a flag will show the name and status of each network interface.

pluto requires a database of preshared secrets and RSA private keys. This is described in the ipsec.secrets(5). pluto is told of RSA public keys via whack commands. If the connection is Opportunistic, and no RSA public key is known, pluto will attempt to fetch RSA keys using the Domain Name System.  

Setting up KLIPS for pluto

The most basic network topology that pluto supports has two security gateways negotiating on behalf of client subnets. The diagram of RGB's testbed is a good example (see klips/doc/rgb_setup.txt).

The file INSTALL in the base directory of this distribution explains how to start setting up the whole system, including KLIPS.

Make sure that the security gateways have routes to each other. This is usually covered by the default route, but may require issuing route(8) commands. The route must go through a particular IP interface (we will assume it is eth0, but it need not be). The interface that connects the security gateway to its client must be a different one.

It is necessary to issue a ipsec_tncfg(8) command on each gateway. The required command is:

   ipsec tncfg --attach --virtual ipsec0 --physical eth0

A command to set up the ipsec0 virtual interface will also need to be run. It will have the same parameters as the command used to set up the physical interface to which it has just been connected using ipsec_tncfg(8).  

ipsec.secrets file

A pluto daemon and another IKE daemon (for example, another instance of pluto) must convince each other that they are who they are supposed to be before any negotiation can succeed. This authentication is accomplished by using either secrets that have been shared beforehand (manually) or by using RSA signatures. There are other techniques, but they have not been implemented in pluto.

The file /etc/ipsec.secrets is used to keep preshared secret keys and RSA private keys for authentication with other IKE daemons. For debugging, there is an argument to the pluto command to use a different file. This file is described in ipsec.secrets(5).  

Running Pluto

To fire up the daemon, just type pluto (be sure to be running as the superuser). The default IKE port number is 500, the UDP port assigned by IANA for IKE Daemons. pluto must be run by the superuser to be able to use the UDP 500 port.

pluto attempts to create a lockfile with the name /var/run/ If the lockfile cannot be created, pluto exits - this prevents multiple plutos from competing Any ``leftover'' lockfile must be removed before pluto will run. pluto writes its pid into this file so that scripts can find it. This lock will not function properly if it is on an NFS volume (but sharing locks on multiple machines doesn't make sense anyway).

pluto then forks and the parent exits. This is the conventional ``daemon fork''. It can make debugging awkward, so there is an option to suppress this fork.

All logging, including diagnostics, is sent to syslog(3) with facility=authpriv; it decides where to put these messages (possibly in /var/log/secure). Since this too can make debugging awkward, there is an option to steer logging to stderr.

If the --perpeerlog option is given, then pluto will open a log file per connection. By default, this is in /var/log/pluto/peer, in a subdirectory formed by turning all dot (.) [IPv4} or colon (:) [IPv6] into slashes (/).

The base directory can be changed with the --perpeerlogbase.

Once pluto is started, it waits for requests from whack.  

Pluto's Internal State

To understand how to use pluto, it is helpful to understand a little about its internal state. Furthermore, the terminology is needed to decipher some of the diagnostic messages.

The (potential) connection database describes attributes of a connection. These include the IP addresses of the hosts and client subnets and the security characteristics desired. pluto requires this information (simply called a connection) before it can respond to a request to build an SA. Each connection is given a name when it is created, and all references are made using this name.

During the IKE exchange to build an SA, the information about the negotiation is represented in a state object. Each state object reflects how far the negotiation has reached. Once the negotiation is complete and the SA established, the state object remains to represent the SA. When the SA is terminated, the state object is discarded. Each State object is given a serial number and this is used to refer to the state objects in logged messages.

Each state object corresponds to a connection and can be thought of as an instantiation of that connection. At any particular time, there may be any number of state objects corresponding to a particular connection. Often there is one representing an ISAKMP SA and another representing an IPsec SA.

KLIPS hooks into the routing code in a LINUX kernel. Traffic to be processed by an IPsec SA must be directed through KLIPS by routing commands. Furthermore, the processing to be done is specified by ipsec eroute(8) commands. pluto takes the responsibility of managing both of these special kinds of routes.

Each connection may be routed, and must be while it has an IPsec SA. The connection specifies the characteristics of the route: the interface on this machine, the ``gateway'' (the nexthop), and the peer's client subnet. Two connections may not be simultaneously routed if they are for the same peer's client subnet but use different interfaces or gateways (pluto's logic does not reflect any advanced routing capabilities).

Each eroute is associated with the state object for an IPsec SA because it has the particular characteristics of the SA. Two eroutes conflict if they specify the identical local and remote clients (unlike for routes, the local clients are taken into account).

When pluto needs to install a route for a connection, it must make sure that no conflicting route is in use. If another connection has a conflicting route, that route will be taken down, as long as there is no IPsec SA instantiating that connection. If there is such an IPsec SA, the attempt to install a route will fail.

There is an exception. If pluto, as Responder, needs to install a route to a fixed client subnet for a connection, and there is already a conflicting route, then the SAs using the route are deleted to make room for the new SAs. The rationale is that the new connection is probably more current. The need for this usually is a product of Road Warrior connections (these are explained later; they cannot be used to initiate).

When pluto needs to install an eroute for an IPsec SA (for a state object), first the state object's connection must be routed (if this cannot be done, the eroute and SA will not be installed). If a conflicting eroute is already in place for another connection, the eroute and SA will not be installed (but note that the routing exception mentioned above may have already deleted potentially conflicting SAs). If another IPsec SA for the same connection already has an eroute, all its outgoing traffic is taken over by the new eroute. The incoming traffic will still be processed. This characteristic is exploited during rekeying.

All of these routing characteristics are expected change when KLIPS is modified to use the firewall hooks in the LINUX 2.4.x kernel.  

Using Whack

whack is used to command a running pluto. whack uses a UNIX domain socket to speak to pluto (by default, /var/pluto.ctl).

whack has an intricate argument syntax. This syntax allows many different functions to be specified. The help form shows the usage or version information. The connection form gives pluto a description of a potential connection. The public key form informs pluto of the RSA public key for a potential peer. The delete form deletes a connection description and all SAs corresponding to it. The listen form tells pluto to start or stop listening on the public interfaces for IKE requests from peers. The route form tells pluto to set up routing for a connection; the unroute form undoes this. The initiate form tells pluto to negotiate an SA corresponding to a connection. The terminate form tells pluto to remove all SAs corresponding to a connection, including those being negotiated. The status form displays the pluto's internal state. The debug form tells pluto to change the selection of debugging output ``on the fly''. The shutdown form tells pluto to shut down, deleting all SAs.

Most options are specific to one of the forms, and will be described with that form. There are three options that apply to all forms.

--ctlbase path
path.ctl is used as the UNIX domain socket for talking to pluto. This option facilitates debugging.
--optionsfrom filename
adds the contents of the file to the argument list.
--label string
adds the string to all error messages generated by whack.

The help form of whack is self-explanatory.

display the usage message.
display the version of whack.

The connection form describes a potential connection to pluto. pluto needs to know what connections can and should be negotiated. When pluto is the initiator, it needs to know what to propose. When pluto is the responder, it needs to know enough to decide whether is is willing to set up the proposed connection.

The description of a potential connection can specify a large number of details. Each connection has a unique name. This name will appear in a updown shell command, so it should not contain punctuation that would make the command ill-formed.

--name connection-name

The topology of a connection is symmetric, so to save space here is half a picture:


A similar trick is used in the flags. The same flag names are used for both ends. Those before the --to flag describe the left side and those afterwards describe the right side. When pluto attempts to use the connection, it decides whether it is the left side or the right side of the connection, based on the IP numbers of its interfaces.

--id id
the identity of the end. Currently, this can be an IP address (specified as dotted quad or as a Fully Qualified Domain Name, which will be resolved immediately) or as a Fully Qualified Domain Name itself (prefixed by ``@'' to signify that it should not be resolved), or as user@FQDN, or as the magic value %myid. Pluto only authenticates the identity, and does not use it for addressing, so, for example, an IP address need not be the one to which packets are to be sent. If the option is absent, the identity defaults to the IP address specified by --host. %myid allows the identity to be separately specified (by the pluto or whack option --myid or by the ipsec.conf(5) config setup parameter myid). Otherwise, pluto tries to guess what %myid should stand for: the IP address of %defaultroute, if it is supported by a suitable TXT record in the reverse domain for that IP address, or the system's hostname, if it is supported by a suitable TXT record in its forward domain.
--host ip-address
--host %any
--host %opportunistic
the IP address of the end (generally the public interface). If pluto is to act as a responder for IKE negotiations initiated from unknown IP addresses (the ``Road Warrior'' case), the IP address should be specified as %any (currently, the obsolete notation is also accepted for this). If pluto is to opportunistically initiate the connection, use %opportunistic
--ikeport port-number
the UDP port that IKE listens to on that host. The default is 500. (pluto on this machine uses the port specified by its own command line argument, so this only affects where pluto sends messages.)
--nexthop ip-address
where to route packets for the peer's client (presumably for the peer too, but it will not be used for this). When pluto installs an IPsec SA, it issues a route command. It uses the nexthop as the gateway. The default is the peer's IP address (this can be explicitly written as %direct; the obsolete notation is accepted). This option is necessary if pluto's host's interface used for sending packets to the peer is neither point-to-point nor directly connected to the peer.
--client subnet
the subnet for which the IPsec traffic will be destined. If not specified, the host will be the client. The subnet can be specified in any of the forms supported by ipsec_atosubnet(3). The general form is address/mask. The address can be either a domain name or four decimal numbers (specifying octets) separated by dots. The most convenient form of the mask is a decimal integer, specifying the number of leading one bits in the mask. So, for example, would specify the class A network ``Net 10''.
specifies that when an RSA public key is needed to authenticate this host, and it isn't already known, fetch it from DNS.
--updown updown
specifies an external shell command to be run whenever pluto brings up or down a connection. The script is used to build a shell command, so it may contain positional parameters, but ought not to have punctuation that would cause the resulting command to be ill-formed. The default is ipsec _updown.
separates the specification of the left and right ends of the connection.

The potential connection description also specifies characteristics of rekeying and security.

Propose and allow preshared secret authentication for IKE peers. This authentication requires that each side use the same secret. May be combined with --rsasig; at least one must be specified.
Propose and allow RSA signatures for authentication of IKE peers. This authentication requires that each side have have a private key of its own and know the public key of its peer. May be combined with --psk; at least one must be specified.
All proposed or accepted IPsec SAs will include non-null ESP. The actual choices of transforms are wired into pluto.
All proposed IPsec SAs will include IPCOMP (compression). This will be ignored if KLIPS is not configured with IPCOMP support.
the IPsec SA should use tunneling. Implicit if the SA is for clients. Must only be used with --authenticate or --encrypt.
The host addresses will be interpreted as IPv4 addresses. This is the default. Note that for a connection, all host addresses must be of the same Address Family (IPv4 and IPv6 use different Address Families).
The host addresses (including nexthop) will be interpreted as IPv6 addresses. Note that for a connection, all host addresses must be of the same Address Family (IPv4 and IPv6 use different Address Families).
The client addresses will be interpreted as IPv4 addresses. The default is to match what the host will be. This does not imply --tunnel so the flag can be safely used when no tunnel is actually specified. Note that for a connection, all tunnel addresses must be of the same Address Family.
The client addresses will be interpreted as IPv6 addresses. The default is to match what the host will be. This does not imply --tunnel so the flag can be safely used when no tunnel is actually specified. Note that for a connection, all tunnel addresses must be of the same Address Family.
There should be Perfect Forward Secrecy - new keying material will be generated for each IPsec SA rather than being derived from the ISAKMP SA keying material. Since the group to be used cannot be negotiated (a dubious feature of the standard), pluto will propose the same group that was used during Phase 1. We don't implement a stronger form of PFS which would require that the ISAKMP SA be deleted after the IPSEC SA is negotiated.
If the connection is a tunnel, allow packets arriving through the tunnel to have any source and destination addresses.

If none of the --encrypt, --authenticate, --compress, or --pfs flags is given, the initiating the connection will only build an ISAKMP SA. For such a connection, client subnets have no meaning and must not be specified.

More work is needed to allow for flexible policies. Currently policy is hardwired in the source file spdb.c. The ISAKMP SAs may use Oakley groups MODP1024 and MODP1536; 3DES encryption; SHA1-96 and MD5-96 authentication. The IPsec SAs may use 3DES and MD5-96 or SHA1-96 for ESP. IPCOMP Compression is always Deflate.

--ikelifetime seconds
how long pluto will propose that an ISAKMP SA be allowed to live. The default is 3600 (one hour) and the maximum is 28800 (8 hours). This option will not affect what is accepted. pluto will reject proposals that exceed the maximum.
--ipseclifetime seconds
how long pluto will propose that an IPsec SA be allowed to live. The default is 28800 (eight hours) and the maximum is 86400 (one day). This option will not affect what is accepted. pluto will reject proposals that exceed the maximum.
--rekeymargin seconds
how long before an SA's expiration should pluto try to negotiate a replacement SA. This will only happen if pluto was the initiator. The default is 540 (nine minutes).
--rekeyfuzz percentage
maximum size of random component to add to rekeymargin, expressed as a percentage of rekeymargin. pluto will select a delay uniformly distributed within this range. By default, the percentage will be 100. If greater determinism is desired, specify 0. It may be appropriate for the percentage to be much larger than 100.
--keyingtries count
how many times pluto should try to negotiate an SA, either for the first time or for rekeying. A value of 0 is interpreted as a very large number: never give up. The default is three.
A misnomer. Only rekey a connection if we were the Initiator and there was recent traffic on the existing connection. This applies to Phase 1 and Phase 2. This is currently the only automatic way for a connection to terminate. It may be useful with Road Warrior or Opportunistic connections.
Since SA lifetime negotiation is take-it-or-leave it, a Responder normally uses the shorter of the negotiated or the configured lifetime. This only works because if the lifetime is shorter than negotiated, the Responder will rekey in time so that everything works. This interacts badly with --dontrekey. In this case, the Responder will end up rekeying to rectify a shortfall in an IPsec SA lifetime; for an ISAKMP SA, the Responder will accept the negotiated lifetime.
when used in the connection form, it causes any previous connection with this name to be deleted before this one is added. Unlike a normal delete, no diagnostic is produced if there was no previous connection to delete. Any routing in place for the connection is undone.

The delete form deletes a named connection description and any SAs established or negotiations initiated using this connection. Any routing in place for the connection is undone.

--name connection-name

The deletestate form deletes the state object with the specified serial number. This is useful for selectively deleting instances of connections.

--deletestate state-number

The route form of the whack command tells pluto to set up routing for a connection. Although like a traditional route, it uses an ipsec device as a virtual interface. Once routing is set up, no packets will be sent ``in the clear'' to the peer's client specified in the connection. A TRAP shunt eroute will be installed; if outbound traffic is caught, Pluto will initiate the connection. An explicit whack route is not always needed: if it hasn't been done when an IPsec SA is being installed, one will be automatically attempted.

When a routing is attempted for a connection, there must not already be a routing for a different connection with the same subnet but different interface or destination, or if there is, it must not be being used by an IPsec SA. Otherwise the attempt will fail.

--name connection-name

The unroute form of the whack command tells pluto to undo a routing. pluto will refuse if an IPsec SA is using the connection. If another connection is sharing the same routing, it will be left in place. Without a routing, packets will be sent without encryption or authentication.

--name connection-name

The initiate form tells pluto to initiate a negotiation with another pluto (or other IKE daemon) according to the named connection. Initiation requires a route that --route would provide; if none is in place at the time an IPsec SA is being installed, pluto attempts to set one up.

--name connection-name

The initiate form of the whack command will relay back from pluto status information via the UNIX domain socket (unless --asynchronous is specified). The status information is meant to look a bit like that from FTP. Currently whack simply copies this to stderr. When the request is finished (eg. the SAs are established or pluto gives up), pluto closes the channel, causing whack to terminate.

The opportunistic initiate form is mainly used for debugging.

--oppohere ip-address
--oppothere ip-address

This will cause pluto to attempt to opportunistically initiate a connection from here to the there, even if a previous attempt had been made. The whack log will show the progress of this attempt.

The terminate form tells pluto to delete any SAs that use the specified connection and to stop any negotiations in process. It does not prevent new negotiations from starting (the delete form has this effect).

--name connection-name

The public key for informs pluto of the RSA public key for a potential peer. Private keys must be kept secret, so they are kept in ipsec.secrets(5).

--keyid id
specififies the identity of the peer for which a public key should be used. Its form is identical to the identity in the connection. If no public key is specified, pluto attempts to find KEY records from DNS for the id (if a FQDN) or through reverse lookup (if an IP address). Note that there several interesting ways in which this is not secure.
specifies that the new key is added to the collection; otherwise the new key replaces any old ones.
--pubkeyrsa key
specifies the value of the RSA public key. It is a sequence of bytes as described in RFC 2537 ``RSA/MD5 KEYs and SIGs in the Domain Name System (DNS)''. It is denoted in a way suitable for ipsec_ttodata(3). For example, a base 64 numeral starts with 0s.

The listen form tells pluto to start listening for IKE requests on its public interfaces. To avoid race conditions, it is normal to load the appropriate connections into pluto before allowing it to listen. If pluto isn't listening, it is pointless to initiate negotiations, so it will refuse requests to do so. Whenever the listen form is used, pluto looks for public interfaces and will notice when new ones have been added and when old ones have been removed. This is also the trigger for pluto to read the ipsec.secrets file. So listen may useful more than once.

start listening for IKE traffic on public interfaces.
stop listening for IKE traffic on public interfaces.

The status form will display information about the internal state of pluto: information about each potential connection, about each state object, and about each shunt that pluto is managing without an associated connection.


The shutdown form is the proper way to shut down pluto. It will tear down the SAs on this machine that pluto has negotiated. It does not inform its peers, so the SAs on their machines remain.



It would be normal to start pluto in one of the system initialization scripts. It needs to be run by the superuser. Generally, no arguments are needed. To run in manually, the superuser can simply type

   ipsec pluto

The command will immediately return, but a pluto process will be left running, waiting for requests from whack or a peer.

Using whack, several potential connections would be described:

   ipsec whack --name silly --host --to --host --ikelifetime 900 --ipseclifetime 800 --keyingtries 3

Since this silly connection description specifies neither encryption, authentication, nor tunneling, it could only be used to establish an ISAKMP SA.
   ipsec whack --name secret --host --client --to --host --client --encrypt

This is something that must be done on both sides. If the other side is pluto, the same whack command could be used on it (the command syntax is designed to not distinguish which end is ours).

Now that the connections are specified, pluto is ready to handle requests and replies via the public interfaces. We must tell it to discover those interfaces and start accepting messages from peers:

   ipsec whack --listen

If we don't immediately wish to bring up a secure connection between the two clients, we might wish to prevent insecure traffic. The routing form asks pluto to cause the packets sent from our client to the peer's client to be routed through the ipsec0 device; if there is no SA, they will be discarded:

   ipsec whack --route secret

Finally, we are ready to get pluto to initiate negotiation for an IPsec SA (and implicitly, an ISAKMP SA):

   ipsec whack --initiate --name secret

A small log of interesting events will appear on standard output (other logging is sent to syslog).

whack can also be used to terminate pluto cleanly, tearing down all SAs that it has negotiated.

   ipsec whack --shutdown

Notification of any IPSEC SA deletion, but not ISAKMP SA deletion is sent to the peer. Unfortunately, such Notification is not reliable. Furthermore, pluto itself ignores Notifications.  

The updown command

Whenever pluto brings a connection up or down, it invokes the updown command. This command is specified using the --updown option. This allows for customized control over routing and firewall manipulation.

The updown is invoked for five different operations. Each of these operations can be for our client subnet or for our host itself.

prepare-host or prepare-client
is run before bringing up a new connection if no other connection with the same clients is up. Generally, this is useful for deleting a route that might have been set up before pluto was run or perhaps by some agent not known to pluto.
route-host or route-client
is run when bringing up a connection for a new peer client subnet (even if prepare-host or prepare-client was run). The command should install a suitable route. Routing decisions are based only on the destination (peer's client) subnet address, unlike eroutes which discriminate based on source too.
unroute-host or unroute-client
is run when bringing down the last connection for a particular peer client subnet. It should undo what the route-host or route-client did.
up-host or up-client
is run when bringing up a tunnel eroute with a pair of client subnets that does not already have a tunnel eroute. This command should install firewall rules as appropriate. It is generally a good idea to allow IKE messages (UDP port 500) travel between the hosts.
down-host or down-client
is run when bringing down the eroute for a pair of client subnets. This command should delete firewall rules as appropriate. Note that there may remain some inbound IPsec SAs with these client subnets.

The script is passed a large number of environment variables to specify what needs to be done.

indicates what version of this interface is being used. This document describes version 1.1. This is upwardly compatible with version 1.0.
specifies the name of the operation to be performed (prepare-host,r prepare-client, up-host, up-client, down-host, or down-client). If the address family for security gateway to security gateway communications is IPv6, then a suffix of -v6 is added to the verb.
is the name of the connection for which we are routing.
is the next hop to which packets bound for the peer must be sent.
is the name of the ipsec interface to be used.
is the IP address of our host.
is the IP address / count of our client subnet. If the client is just the host, this will be the host's own IP address / max (where max is 32 for IPv4 and 128 for IPv6).
is the IP address of our client net. If the client is just the host, this will be the host's own IP address.
is the mask for our client net. If the client is just the host, this will be
is the IP address of our peer.
is the IP address / count of the peer's client subnet. If the client is just the peer, this will be the peer's own IP address / max (where max is 32 for IPv4 and 128 for IPv6).
is the IP address of the peer's client net. If the client is just the peer, this will be the peer's own IP address.
is the mask for the peer's client net. If the client is just the peer, this will be

All output sent by the script to stderr or stdout is logged. The script should return an exit status of 0 if and only if it succeeds.

Pluto waits for the script to finish and will not do any other processing while it is waiting. The script may assume that pluto will not change anything while the script runs. The script should avoid doing anything that takes much time and it should not issue any command that requires processing by pluto. Either of these activities could be performed by a background subprocess of the script.  


When an SA that was initiated by pluto has only a bit of lifetime left, pluto will initiate the creation of a new SA. This applies to ISAKMP and IPsec SAs. The rekeying will be initiated when the SA's remaining lifetime is less than the rekeymargin plus a random percentage, between 0 and rekeyfuzz, of the rekeymargin.

Similarly, when an SA that was initiated by the peer has only a bit of lifetime left, pluto will try to initiate the creation of a replacement. To give preference to the initiator, this rekeying will only be initiated when the SA's remaining lifetime is half of rekeymargin. If rekeying is done by the responder, the roles will be reversed: the responder for the old SA will be the initiator for the replacement. The former initiator might also initiate rekeying, so there may be redundant SAs created. To avoid these complications, make sure that rekeymargin is generous.

One risk of having the former responder initiate is that perhaps none of its proposals is acceptable to the former initiator (they have not been used in a successful negotiation). To reduce the chances of this happening, and to prevent loss of security, the policy settings are taken from the old SA (this is the case even if the former initiator is initiating). These may be stricter than those of the connection.

pluto will not rekey an SA if that SA is not the most recent of its type (IPsec or ISAKMP) for its potential connection. This avoids creating redundant SAs.

The random component in the rekeying time (rekeyfuzz) is intended to make certain pathological patterns of rekeying unstable. If both sides decide to rekey at the same time, twice as many SAs as necessary are created. This could become a stable pattern without the randomness.

Another more important case occurs when a security gateway has SAs with many other security gateways. Each of these connections might need to be rekeyed at the same time. This would cause a high peek requirement for resources (network bandwidth, CPU time, entropy for random numbers). The rekeyfuzz can be used to stagger the rekeying times.

Once a new set of SAs has been negotiated, pluto will never send traffic on a superseded one. Traffic will be accepted on an old SA until it expires.  

Selecting a Connection When Responding: Road Warrior Support

When pluto receives an initial Main Mode message, it needs to decide which connection this message is for. It picks based solely on the source and destination IP addresses of the message. There might be several connections with suitable IP addresses, in which case one of them is arbitrarily chosen. (The ISAKMP SA proposal contained in the message could be taken into account, but it is not.)

The ISAKMP SA is negotiated before the parties pass further identifying information, so all ISAKMP SA characteristics specified in the connection description should be the same for every connection with the same two host IP addresses. At the moment, the only characteristic that might differ is authentication method.

Up to this point, all configuring has presumed that the IP addresses are known to all parties ahead of time. This will not work when either end is mobile (or assigned a dynamic IP address for other reasons). We call this situation ``Road Warrior''. It is fairly tricky and has some important limitations, most of which are features of the IKE protocol.

Only the initiator may be mobile: the initiator may have an IP number unknown to the responder. When the responder doesn't recognize the IP address on the first Main Mode packet, it looks for a connection with itself as one end and %any as the other. If it cannot find one, it refuses to negotiate. If it does find one, it creates a temporary connection that is a duplicate except with the %any replaced by the source IP address from the packet; if there was no identity specified for the peer, the new IP address will be used.

When pluto is using one of these temporary connections and needs to find the preshared secret or RSA private key in ipsec.secrets, and and the connection specified no identity for the peer, %any is used as its identity. After all, the real IP address was apparently unknown to the configuration, so it is unreasonable to require that it be used in this table.

Part way into the Phase 1 (Main Mode) negotiation using one of these temporary connection descriptions, pluto will be receive an Identity Payload. At this point, pluto checks for a more appropriate connection, one with an identity for the peer that matches the payload but which would use the same keys so-far used for authentication. If it finds one, it will switch to using this better connection (or a temporary derived from this, if it has %any for the peer's IP address). It may even turn out that no connection matches the newly discovered identity, including the current connection; if so, pluto terminates negotiation.

Unfortunately, if preshared secret authentication is being used, the Identity Payload is encrypted using this secret, so the secret must be selected by the responder without knowing this payload. This limits there to being at most one preshared secret for all Road Warrior systems connecting to a host. RSA Signature authentications does not require that the responder know how to select the initiator's public key until after the initiator's Identity Payload is decoded (using the responder's private key, so that must be preselected).

When pluto is responding to a Quick Mode negotiation via one of these temporary connection descriptions, it may well find that the subnets specified by the initiator don't match those in the temporary connection description. If so, it will look for a connection with matching subnets, its own host address, a peer address of %any and matching identities. If it finds one, a new temporary connection is derived from this one and used for the Quick Mode negotiation of IPsec SAs. If it does not find one, pluto terminates negotiation.

Be sure to specify an appropriate nexthop for the responder to send a message to the initiator: pluto has no way of guessing it (if forwarding isn't required, use an explicit %direct as the nexthop and the IP address of the initiator will be filled in; the obsolete notation is still accepted).

pluto has no special provision for the initiator side. The current (possibly dynamic) IP address and nexthop must be used in defining connections. These must be properly configured each time the initiator's IP address changes. pluto has no mechanism to do this automatically.

Although we call this Road Warrior Support, it could also be used to support encrypted connections with anonymous initiators. The responder's organization could announce the preshared secret that would be used with unrecognized initiators and let anyone connect. Of course the initiator's identity would not be authenticated.

If any Road Warrior connections are supported, pluto cannot reject an exchange initiated by an unknown host until it has determined that the secret is not shared or the signature is invalid. This must await the third Main Mode message from the initiator. If no Road Warrior connection is supported, the first message from an unknown source would be rejected. This has implications for ease of debugging configurations and for denial of service attacks.

Although a Road Warrior connection must be initiated by the mobile side, the other side can and will rekey using the temporary connection it has created. If the Road Warrior wishes to be able to disconnect, it is probably wise to set --keyingtries to 1 in the connection on the non-mobile side to prevent it trying to rekey the connection. Unfortunately, there is no mechanism to unroute the connection automatically.  


pluto accepts several optional arguments, useful mostly for debugging. Except for --interface, each should appear at most once.

--interface interfacename
specifies that the named real public network interface should be considered. The interface name specified should not be ipsecN. If the option doesn't appear, all interfaces are considered. To specify several interfaces, use the option once for each. One use of this option is to specify which interface should be used when two or more share the same IP address.
--ikeport port-number
changes the UDP port that pluto will use (default, specified by IANA: 500)
--ctlbase path
basename for control files. path.ctl is the socket through which whack communicates with pluto. is the lockfile to prevent multiple pluto instances. The default is /var/run/pluto).
--secretsfile file
specifies the file for authentication secrets (default: /etc/ipsec.secrets). This name is subject to ``globbing'' as in sh(1), so every file with a matching name is processed. Quoting is generally needed to prevent the shell from doing the globbing.
--adns pathname
--lwdnsq pathname
specifies where to find pluto's helper program for asynchronous DNS lookup. pluto can be built to use one of two helper programs: _pluto_adns or lwdnsq. You must use the program for which it was built. By default, pluto will look for the program in $IPSEC_DIR (if that environment variable is defined) or, failing that, in the same directory as pluto.
disable ``daemon fork'' (default is to fork). In addition, after the lock file and control socket are created, print the line ``Pluto initialized'' to standard out.
don't actually implement negotiated IPsec SAs
if this option has been selected, whenever a new ISAKMP SA is established, any connection with the same Peer ID but a different Peer IP address is unoriented (causing all its SAs to be deleted). This helps clean up dangling SAs when a connection is lost and then regained at another IP address.
log goes to standard out {default is to use syslogd(8))

For example

pluto --secretsfile ipsec.secrets --ctlbase pluto.base --ikeport 8500 --nofork --noklips --stderrlog

lets one test pluto without using the superuser account.

pluto is willing to produce a prodigious amount of debugging information. To do so, it must be compiled with -DDEBUG. There are several classes of debugging output, and pluto may be directed to produce a selection of them. All lines of debugging output are prefixed with ``| '' to distinguish them from error messages.

When pluto is invoked, it may be given arguments to specify which classes to output. The current options are:

show the raw bytes of messages
show the encryption and decryption of messages
show the structure of input messages
show the structure of output messages
show pluto's decision making
[this option is temporary] log more detail of lifecycle of SAs
show pluto's interaction with KLIPS
show pluto's interaction with DNS for KEY and TXT records
show why pluto didn't find a suitable DNS TXT record to authorize opportunistic initiation
all of the above
allow debugging output with private keys.
none of the above

The debug form of the whack command will change the selection in a running pluto. If a connection name is specified, the flags are added whenever pluto has identified that it is dealing with that connection. Unfortunately, this is often part way into the operation being observed.

For example, to start a pluto with a display of the structure of input and output:

pluto --debug-emitting --debug-parsing

To later change this pluto to only display raw bytes:

whack --debug-raw

For testing, SSH's IKE test page is quite useful:

Hint: ISAKMP SAs are often kept alive by IKEs even after the IPsec SA is established. This allows future IPsec SA's to be negotiated directly. If one of the IKEs is restarted, the other may try to use the ISAKMP SA but the new IKE won't know about it. This can lead to much confusion. pluto is not yet smart enough to get out of such a mess.  

Pluto's Behaviour When Things Go Wrong

When pluto doesn't understand or accept a message, it just ignores the message. It is not yet capable of communicating the problem to the other IKE daemon (in the future it might use Notifications to accomplish this in many cases). It does log a diagnostic.

When pluto gets no response from a message, it resends the same message (a message will be sent at most three times). This is appropriate: UDP is unreliable.

When pluto gets a message that it has already seen, there are many cases when it notices and discards it. This too is appropriate for UDP.

Combine these three rules, and you can explain many apparently mysterious behaviours. In a pluto log, retrying isn't usually the interesting event. The critical thing is either earlier (pluto got a message which it didn't like and so ignored, so it was still awaiting an acceptable message and got impatient) or on the other system (pluto didn't send a reply because it wasn't happy with the previous message).  


If pluto is compiled without -DKLIPS, it negotiates Security Associations but never ask the kernel to put them in place and never makes routing changes. This allows pluto to be tested on systems without KLIPS, but makes it rather useless.

Each IPsec SA is assigned an SPI, a 32-bit number used to refer to the SA. The IKE protocol lets the destination of the SA choose the SPI. The range 0 to 0xFF is reserved for IANA. Pluto also avoids choosing an SPI in the range 0x100 to 0xFFF, leaving these SPIs free for manual keying. Remember that the peer, if not pluto, may well chose SPIs in this range.  


This catalogue of policies may be of use when trying to configure Pluto and another IKE implementation to interoperate.

In Phase 1, only Main Mode is supported. We are not sure that Aggressive Mode is secure. For one thing, it does not support identity protection. It may allow more severe Denial Of Service attacks.

No Informational Exchanges are supported. These are optional and since their delivery is not assured, they must not matter. It is the case that some IKE implementations won't interoperate without Informational Exchanges, but we feel they are broken.

No Informational Payloads are supported. These are optional, but useful. It is of concern that these payloads are not authenticated in Phase 1, nor in those Phase 2 messages authenticated with HASH(3).

Diffie Hellman Groups MODP 1024 and MODP 1536 (2 and 5) are supported. Group MODP768 (1) is not supported because it is too weak.
Host authetication can be done by RSA Signatures or Pre-Shared Secrets.
3DES CBC (Cypher Block Chaining mode) is the only encryption supported, both for ISAKMP SAs and IPSEC SAs.
MD5 and SHA1 hashing are supported for packet authentication in both kinds of SAs.
Only ESP is supported; it must include authentication.
Each of these may be combined with IPCOMP Deflate compression, but only if the potential connection specifies compression and only if KLIPS is configured with IPCOMP support.
The IPSEC SAs must be tunnel mode.
When responding to an ISAKMP SA proposal, the maximum acceptable lifetime is eight hours. The default is one hour. There is no minimum. The --ikelifetime flag controls this when pluto is initiating.
When responding to an IPSEC SA proposal, the maximum acceptable lifetime is one day. The default is eight hours. There is no minimum. The --ipseclifetime flag controls this when pluto is initiating.
PFS is acceptable, and will be proposed if the --pfs flag was specified. The DH group proposed will be the same as negotiated for Phase 1.


Pluto responds to SIGHUP by issuing a suggestion that ``whack --listen'' might have been intended.

Pluto exits when it recieves SIGTERM.  


pluto normally forks a daemon process, so the exit status is normally a very preliminary result.

means that all is OK so far.
means that something was wrong.
means that the lock file already exists.

If whack detects a problem, it will return an exit status of 1. If it received progress messages from pluto, it returns as status the value of the numeric prefix from the last such message that was not a message sent to syslog or a comment (but the prefix for success is treated as 0). Otherwise, the exit status is 0.  






The rest of the FreeS/WAN distribution, in particular ipsec(8).

ipsec_auto(8) is designed to make using pluto more pleasant. Use it!

ipsec.secrets(5) describes the format of the secrets file.

ipsec_atoaddr(3), part of the FreeS/WAN distribution, describes the forms that IP addresses may take. ipsec_atosubnet(3), part of the FreeS/WAN distribution, describes the forms that subnet specifications.

For more information on IPsec, the mailing list, and the relevant documents, see:

At the time of writing, the most relevant IETF RFCs are:

RFC2409 The Internet Key Exchange (IKE)
RFC2408 Internet Security Association and Key Management Protocol (ISAKMP)
RFC2407 The Internet IP Security Domain of Interpretation for ISAKMP

The FreeS/WAN web site <htp://> and the mailing lists described there.  


This code is released under the GPL terms. See the accompanying file COPYING-2.0 for more details. The GPL does NOT apply to those pieces of code written by others which are included in this distribution, except as noted by the individual authors.

This software was originally written for the FreeS/WAN project <> by Angelos D. Keromytis (, in May/June 1997, in Athens, Greece. Thanks go to John Ioannidis for his help.

It is currently (2000) being developed and maintained by D. Hugh Redelmeier (, in Canada. The regulations of Greece and Canada allow us to make the code freely redistributable.

Kai Martius ( contributed the initial version of the code supporting PFS.

Richard Guy Briggs <> and Peter Onion <> added the PFKEY2 support.

We gratefully acknowledge that we use parts of Eric Young's libdes package; see ../libdes/COPYRIGHT.  


pluto is a work-in-progress. It currently has many limitations. For example, it ignores notification messages that it receives, and it generates only Delete Notifications and those only for IPSEC SAs.

pluto does not support the Commit Flag. The Commit Flag is a bad feature of the IKE protocol. It isn't protected -- neither encrypted nor authenticated. A man in the middle could turn it on, leading to DoS. We just ignore it, with a warning. This should let us interoperate with implementations that insist on it, with minor damage.

pluto does not check that the SA returned by the Responder is actually one that was proposed. It only checks that the SA is acceptable. The difference is not large, but can show up in attributes such as SA lifetime.

There is no good way for a connection to be automatically terminated. This is a problem for Road Warrior and Opportunistic connections. The --dontrekey option does prevent the SAs from being rekeyed on expiry. Additonally, if a Road Warrior connection has a client subnet with a fixed IP address, a negotiation with that subnet will cause any other connection instantiations with that same subnet to be unoriented (deleted, in effect). See also the --uniqueids option for an extension of this.

When pluto sends a message to a peer that has disappeared, pluto receives incomplete information from the kernel, so it logs the unsatisfactory message ``some IKE message we sent has been rejected with ECONNREFUSED (kernel supplied no details)''. John Denker suggests that this command is useful for tracking down the source of these problems:
       tcpdump -i eth0 icmp[0] != 8 and icmp[0] != 0

Substitute your public interface for eth0 if it is different.

The word ``authenticate'' is used for two different features. We must authenticate each IKE peer to the other. This is an important task of Phase 1. Each packet must be authenticated, both in IKE and in IPsec, and the method for IPsec is negotiated as part of an ESP SA. Unfortunately, the protocol has no mechanism for authenticating the Phase 2 identities.

Bugs should be reported to the <> mailing list. Caution: we cannot accept actual code from US residents, or even US citizens living outside the US, because that would bring FreeS/WAN under US export law. Some other countries cause similar problems. In general, we would prefer that you send detailed problem reports rather than code: we want FreeS/WAN to be unquestionably freely exportable, which means being very careful about where the code comes from, and for a small bug fix, that is often more time-consuming than just reinventing the fix ourselves.



IKE's Job
Before Running Pluto
Setting up KLIPS for pluto
ipsec.secrets file
Running Pluto
Pluto's Internal State
Using Whack
The updown command
Selecting a Connection When Responding: Road Warrior Support
Pluto's Behaviour When Things Go Wrong

This document was created by man2html, using the manual pages.
Time: 19:04:25 GMT, April 17, 2004