diff --git a/cli/testdata/coder_--help.golden b/cli/testdata/coder_--help.golden
index 6881d4320f098..915c8362f01b8 100644
--- a/cli/testdata/coder_--help.golden
+++ b/cli/testdata/coder_--help.golden
@@ -45,7 +45,7 @@ Workspace Commands:
   ssh            Start a shell into a workspace
   start          Start a workspace
   stop           Stop a workspace
-  update         Update a workspace
+  update         Will update and start a given workspace if it is out of date.
 
 Flags:
       --global-config coder   Path to the global coder config directory.
diff --git a/cli/testdata/coder_update_--help.golden b/cli/testdata/coder_update_--help.golden
index 85ae220fdd5c1..d6e4ab61e0730 100644
--- a/cli/testdata/coder_update_--help.golden
+++ b/cli/testdata/coder_update_--help.golden
@@ -1,4 +1,4 @@
-Update a workspace
+Will update and start a given workspace if it is out of date. Use --always-prompt to change the parameter values of the workspace.
 
 Usage:
   coder update <workspace> [flags]
diff --git a/cli/update.go b/cli/update.go
index 9e23ee73569dd..4e25893119374 100644
--- a/cli/update.go
+++ b/cli/update.go
@@ -20,7 +20,9 @@ func update() *cobra.Command {
 		Annotations: workspaceCommand,
 		Use:         "update <workspace>",
 		Args:        cobra.ExactArgs(1),
-		Short:       "Update a workspace",
+		Short:       "Will update and start a given workspace if it is out of date.",
+		Long: "Will update and start a given workspace if it is out of date. Use --always-prompt to change " +
+			"the parameter values of the workspace.",
 		RunE: func(cmd *cobra.Command, args []string) error {
 			client, err := CreateClient(cmd)
 			if err != nil {
@@ -68,7 +70,7 @@ func update() *cobra.Command {
 
 			build, err := client.CreateWorkspaceBuild(cmd.Context(), workspace.ID, codersdk.CreateWorkspaceBuildRequest{
 				TemplateVersionID:   template.ActiveVersionID,
-				Transition:          workspace.LatestBuild.Transition,
+				Transition:          codersdk.WorkspaceTransitionStart,
 				ParameterValues:     buildParams.parameters,
 				RichParameterValues: buildParams.richParameters,
 			})
diff --git a/docs/cli.md b/docs/cli.md
index 0c749c3de21a9..45e25013cf4e1 100644
--- a/docs/cli.md
+++ b/docs/cli.md
@@ -50,6 +50,6 @@ coder [flags]
 | [<code>stop</code>](./cli/coder_stop)                     | Stop a workspace                                                |
 | [<code>templates</code>](./cli/coder_templates)           | Manage templates                                                |
 | [<code>tokens</code>](./cli/coder_tokens)                 | Manage personal access tokens                                   |
-| [<code>update</code>](./cli/coder_update)                 | Update a workspace                                              |
+| [<code>update</code>](./cli/coder_update)                 | Will update and start a given workspace if it is out of date.   |
 | [<code>users</code>](./cli/coder_users)                   | Manage users                                                    |
 | [<code>version</code>](./cli/coder_version)               | Show coder version                                              |
diff --git a/docs/cli/coder_update.md b/docs/cli/coder_update.md
index f398650cae592..92da1c1c291e5 100644
--- a/docs/cli/coder_update.md
+++ b/docs/cli/coder_update.md
@@ -2,7 +2,7 @@
 
 # coder update
 
-Update a workspace
+Will update and start a given workspace if it is out of date. Use --always-prompt to change the parameter values of the workspace.
 
 ## Usage