diff --git a/src/main/java/com/xebialabs/overthere/ssh/SshConnection.java b/src/main/java/com/xebialabs/overthere/ssh/SshConnection.java
index d4c6166b..5f41803f 100644
--- a/src/main/java/com/xebialabs/overthere/ssh/SshConnection.java
+++ b/src/main/java/com/xebialabs/overthere/ssh/SshConnection.java
@@ -62,15 +62,7 @@
 import static com.xebialabs.overthere.ConnectionOptions.PASSWORD;
 import static com.xebialabs.overthere.ConnectionOptions.PORT;
 import static com.xebialabs.overthere.ConnectionOptions.USERNAME;
-import static com.xebialabs.overthere.ssh.SshConnectionBuilder.ALLOCATE_DEFAULT_PTY;
-import static com.xebialabs.overthere.ssh.SshConnectionBuilder.ALLOCATE_DEFAULT_PTY_DEFAULT;
-import static com.xebialabs.overthere.ssh.SshConnectionBuilder.ALLOCATE_PTY;
-import static com.xebialabs.overthere.ssh.SshConnectionBuilder.CONNECTION_TYPE;
-import static com.xebialabs.overthere.ssh.SshConnectionBuilder.INTERACTIVE_KEYBOARD_AUTH_PROMPT_REGEX;
-import static com.xebialabs.overthere.ssh.SshConnectionBuilder.INTERACTIVE_KEYBOARD_AUTH_PROMPT_REGEX_DEFAULT;
-import static com.xebialabs.overthere.ssh.SshConnectionBuilder.PASSPHRASE;
-import static com.xebialabs.overthere.ssh.SshConnectionBuilder.PRIVATE_KEY_FILE;
-import static com.xebialabs.overthere.ssh.SshConnectionBuilder.SSH_PORT_DEFAULT;
+import static com.xebialabs.overthere.ssh.SshConnectionBuilder.*;
 import static java.net.InetSocketAddress.createUnresolved;
 
 /**
@@ -100,6 +92,8 @@ abstract class SshConnection extends BaseOverthereConnection {
 
     protected final boolean allocateDefaultPty;
 
+    protected final boolean openShellBeforeExecute;
+
     protected String allocatePty;
 
     protected SSHClient sshClient;
@@ -129,6 +123,7 @@ public SshConnection(final String protocol, final ConnectionOptions options, fin
             logger.warn("The " + ALLOCATE_DEFAULT_PTY + " connection option has been deprecated in favour of the " + ALLOCATE_PTY + " option. See https://github.com/xebialabs/overthere#ssh_allocatePty");
         }
         this.allocatePty = options.getOptional(ALLOCATE_PTY);
+        this.openShellBeforeExecute = options.getBoolean(OPEN_SHELL_BEFORE_EXECUTE, OPEN_SHELL_BEFORE_EXECUTE_DEFAULT);
     }
 
     protected void connect() {
@@ -238,6 +233,12 @@ public OverthereProcess startProcess(final CmdLine commandLine) {
 
         CmdLine cmd = processCommandLine(commandLine);
         try {
+            if (openShellBeforeExecute) {
+                logger.debug("Creating a temporary shell to allow for deferred home dir creation.");
+                Session.Shell shell = getSshClient().startSession().startShell();
+                shell.close();
+            }
+
             Session session = getSshClient().startSession();
             if (allocatePty != null && !allocatePty.isEmpty()) {
                 if (allocateDefaultPty) {
diff --git a/src/main/java/com/xebialabs/overthere/ssh/SshConnectionBuilder.java b/src/main/java/com/xebialabs/overthere/ssh/SshConnectionBuilder.java
index e1a71c96..19c20081 100644
--- a/src/main/java/com/xebialabs/overthere/ssh/SshConnectionBuilder.java
+++ b/src/main/java/com/xebialabs/overthere/ssh/SshConnectionBuilder.java
@@ -192,6 +192,19 @@ public class SshConnectionBuilder implements OverthereConnectionBuilder {
      */
     public static final boolean SUDO_QUOTE_COMMAND_DEFAULT = false;
 
+    /**
+     * Name of the {@link ConnectionOptions connection option} used to specify whether or not to open a shell directly
+     * before executing a remote command. This may be necessary in case a user does not yet have a home directory on a
+     * machine, and this is created for him when he opens a shell.
+     */
+    public static final String OPEN_SHELL_BEFORE_EXECUTE = "openShellBeforeExecute";
+
+    /**
+     * Default value (<code>false</code>) of the {@link ConnectionOptions connection option} used to specify whether or
+     * not to open a shell directory before executing a command.
+     */
+    public static final boolean OPEN_SHELL_BEFORE_EXECUTE_DEFAULT = false;
+
     protected SshConnection connection;
 
     public SshConnectionBuilder(String type, ConnectionOptions options, AddressPortMapper mapper) {