diff --git a/website/content/docs/getting-started/connect-to-target.mdx b/website/content/docs/getting-started/connect-to-target.mdx
index 214c40c86b..f4efb06edd 100644
--- a/website/content/docs/getting-started/connect-to-target.mdx
+++ b/website/content/docs/getting-started/connect-to-target.mdx
@@ -6,28 +6,52 @@ description: |-
   Connecting to your first target
 ---
 
-# Connect to Your First Target
+## Connect to Your First Target
 
-The default target is a TCP target with a default port of `22` (SSH). The host
-sets for this target contain the default host, which has the address
-`127.0.0.1`. When we run `boundary connect` against this target, the single
-available host will be selected and we'll open a local authenticated proxy to
-the target host on the target's default port (`127.0.0.1:22`). Because this
-target is proxying to our local SSH server, we can use our built-in `connect ssh`
-command to wrap the proxied TCP connection and SSH via Boundary:
+The default target is a `tcp` target with a default port of `22` (which
+corresponds to the default SSH port using TCP). The host sets for this target
+contain the default host, which has the address `127.0.0.1`. When we run
+`boundary connect` against this target, the single available host will be
+selected and we'll open a local authenticated proxy to the host on the target's
+default port (`127.0.0.1:22`).
 
 ```
-$ boundary connect ssh -target-id ttcp_1234567890
+$ boundary connect -target-id ttcp_1234567890
 ```
 
-This will execute SSH on the target and port combination specified by the local
-boundary proxy. If you want to specify a username other than your currently
-logged-in user, you can do so via the `-username` flag.
+In the output you'll see the address and port that your SSH client must be told
+to use. In the next section you'll see the `ssh` connect helper in action to
+make it easier to connect to the target with a client.
+
+`boundary connect` has a number of options; one notable option is `-listen-port`
+to choose the port on which the connect command will listen for an incoming
+connection. This can be convenient for allowing Boundary to work with
+applications that allow you to select the address to connect to but not the
+port, but for many applications there are still some extra hurdles that can
+exist, which is why we are building out helpers.
+
+The dev-mode default target allows you to make as many connections as you want
+within the authorized session. When you are finished making connections, simply
+`Ctrl-C/Command-C` the `boundary connect` process to shut down the session.
+
+### Using Connect Helpers
+
+It can be annoying to keep accepting host SSH key prompts as the port changes, much less having to keep
+copying and pasting the current port. To make this easier, Boundary includes
+connect helpers that take care of this work for you. These take the form of
+`boundary connect <subcommand>`. In the following example, the helper will
+automatically execute `ssh` for you, filling in the local address/port, and setting
+an expected host ID so that future connections on different
+automatically-allocated ports don't complain about the host ID changing (you'll
+still need to accept a host key the first time):
+
+```
+$ boundary connect ssh -target-id ttcp_1234567890
+```
 
 If you want to pass additional flags to the SSH client, you can do so by adding
 them to the command line separated by a double-dash; anything after the double
-dash will be passed to the executed client. For instance, rather than using
-`-username`, an equivalent alternative would be:
+dash will be passed to the executed client. For instance:
 
 ```
 $ boundary connect ssh -target-id ttcp_1234567890 -- -l some-other-user
@@ -38,6 +62,13 @@ different style expected by different SSH clients. At the moment, besides `ssh`
 (the default), the `boundary connect ssh` command supports `-style putty` to
 support passing connection information to PuTTY.
 
+One advantage to styles is that Boundary will provide information to the client
+in the format that makes sense. For example, if you want to specify a username
+other than your currently logged-in user, you can do so via the `-username`
+flag. This will ensure that regardless of whether you use the default `ssh`
+style or the `putty` style, the username is properly passed to the executed
+client -- you don't need to figure out the syntax yourself.
+
 ## Selecting Targets
 
 When using `boundary connect` you must identify the target used for connecting.