diff --git a/src/main/kotlin/com/coder/gateway/CoderRemoteConnectionHandle.kt b/src/main/kotlin/com/coder/gateway/CoderRemoteConnectionHandle.kt
index 6fa3ae7a..e976d7d0 100644
--- a/src/main/kotlin/com/coder/gateway/CoderRemoteConnectionHandle.kt
+++ b/src/main/kotlin/com/coder/gateway/CoderRemoteConnectionHandle.kt
@@ -10,6 +10,7 @@ import com.coder.gateway.util.humanizeDuration
 import com.coder.gateway.util.isCancellation
 import com.coder.gateway.util.isWorkerTimeout
 import com.coder.gateway.util.suspendingRetryWithExponentialBackOff
+import com.coder.gateway.cli.CoderCLIManager
 import com.intellij.openapi.application.ApplicationManager
 import com.intellij.openapi.components.service
 import com.intellij.openapi.diagnostic.Logger
@@ -141,7 +142,13 @@ class CoderRemoteConnectionHandle {
             port = 22
             authType = AuthType.OPEN_SSH
         }
-        val accessor = HighLevelHostAccessor.create(credentials, true)
+        val backgroundCredentials = RemoteCredentialsHolder().apply {
+            setHost(CoderCLIManager.getBackgroundHostName(workspace.hostname))
+            userName = "coder"
+            port = 22
+            authType = AuthType.OPEN_SSH
+        }
+        val accessor = HighLevelHostAccessor.create(backgroundCredentials, true)
 
         // Deploy if we need to.
         val ideDir = this.deploy(workspace, accessor, indicator, timeout)
@@ -350,7 +357,7 @@ class CoderRemoteConnectionHandle {
     private fun exec(workspace: WorkspaceProjectIDE, command: String): String {
         logger.info("Running command `$command` in ${workspace.hostname}:${workspace.idePathOnHost}/bin...")
         return ProcessExecutor()
-            .command("ssh", "-t", workspace.hostname, "cd '${workspace.idePathOnHost}' ; cd bin ; $command")
+            .command("ssh", "-t", CoderCLIManager.getBackgroundHostName(workspace.hostname), "cd '${workspace.idePathOnHost}' ; cd bin ; $command")
             .exitValues(0)
             .readOutput(true)
             .execute()
diff --git a/src/main/kotlin/com/coder/gateway/cli/CoderCLIManager.kt b/src/main/kotlin/com/coder/gateway/cli/CoderCLIManager.kt
index 96cb09ea..4691c095 100644
--- a/src/main/kotlin/com/coder/gateway/cli/CoderCLIManager.kt
+++ b/src/main/kotlin/com/coder/gateway/cli/CoderCLIManager.kt
@@ -255,7 +255,7 @@ class CoderCLIManager(
         val startBlock = "# --- START CODER JETBRAINS $host"
         val endBlock = "# --- END CODER JETBRAINS $host"
         val isRemoving = workspaceNames.isEmpty()
-        val proxyArgs =
+        val baseArgs =
             listOfNotNull(
                 escape(localBinaryPath.toString()),
                 "--global-config",
@@ -265,8 +265,9 @@ class CoderCLIManager(
                 "ssh",
                 "--stdio",
                 if (settings.disableAutostart && feats.disableAutostart) "--disable-autostart" else null,
-                if (feats.reportWorkspaceUsage) "--usage-app=jetbrains" else null,
             )
+        val proxyArgs = baseArgs + listOfNotNull(if (feats.reportWorkspaceUsage) "--usage-app=jetbrains" else null)
+        val backgroundProxyArgs = baseArgs + listOfNotNull(if (feats.reportWorkspaceUsage) "--usage-app=disable" else null)
         val extraConfig =
             if (settings.sshConfigOptions.isNotBlank()) {
                 "\n" + settings.sshConfigOptions.prependIndent("  ")
@@ -289,7 +290,19 @@ class CoderCLIManager(
                       SetEnv CODER_SSH_SESSION_TYPE=JetBrains
                     """.trimIndent()
                         .plus(extraConfig)
-                        .replace("\n", System.lineSeparator())
+                        .plus("\n")
+                        .plus(
+                            """
+                            Host ${getBackgroundHostName(deploymentURL, it)}
+                              ProxyCommand ${backgroundProxyArgs.joinToString(" ")} $it
+                              ConnectTimeout 0
+                              StrictHostKeyChecking no
+                              UserKnownHostsFile /dev/null
+                              LogLevel ERROR
+                              SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+                            """.trimIndent()
+                                .plus(extraConfig)
+                        ).replace("\n", System.lineSeparator())
                 },
             )
 
@@ -465,5 +478,20 @@ class CoderCLIManager(
         ): String {
             return "coder-jetbrains--$workspaceName--${url.safeHost()}"
         }
+
+        @JvmStatic
+        fun getBackgroundHostName(
+            url: URL,
+            workspaceName: String,
+        ): String {
+            return getHostName(url, workspaceName) + "--bg"
+        }
+
+        @JvmStatic
+        fun getBackgroundHostName(
+            hostname: String,
+        ): String {
+            return hostname + "--bg"
+        }
     }
 }
diff --git a/src/main/kotlin/com/coder/gateway/views/steps/CoderWorkspaceProjectIDEStepView.kt b/src/main/kotlin/com/coder/gateway/views/steps/CoderWorkspaceProjectIDEStepView.kt
index 334dc460..28bea76a 100644
--- a/src/main/kotlin/com/coder/gateway/views/steps/CoderWorkspaceProjectIDEStepView.kt
+++ b/src/main/kotlin/com/coder/gateway/views/steps/CoderWorkspaceProjectIDEStepView.kt
@@ -214,7 +214,7 @@ class CoderWorkspaceProjectIDEStepView(
                                     } else {
                                         IDECellRenderer(CoderGatewayBundle.message("gateway.connector.view.coder.connect-ssh"))
                                     }
-                                val executor = createRemoteExecutor(CoderCLIManager.getHostName(data.client.url, name))
+                                val executor = createRemoteExecutor(CoderCLIManager.getBackgroundHostName(data.client.url, name))
 
                                 if (ComponentValidator.getInstance(tfProject).isEmpty) {
                                     logger.info("Installing remote path validator...")
diff --git a/src/test/fixtures/outputs/append-blank-newlines.conf b/src/test/fixtures/outputs/append-blank-newlines.conf
index 9c75e87c..022b30b7 100644
--- a/src/test/fixtures/outputs/append-blank-newlines.conf
+++ b/src/test/fixtures/outputs/append-blank-newlines.conf
@@ -4,7 +4,14 @@
 
 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--foo-bar--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio foo-bar
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=jetbrains foo-bar
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--foo-bar--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=disable foo-bar
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/fixtures/outputs/append-blank.conf b/src/test/fixtures/outputs/append-blank.conf
index 566a8522..d04a5c6c 100644
--- a/src/test/fixtures/outputs/append-blank.conf
+++ b/src/test/fixtures/outputs/append-blank.conf
@@ -1,6 +1,13 @@
 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--foo-bar--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio foo-bar
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=jetbrains foo-bar
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--foo-bar--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=disable foo-bar
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/fixtures/outputs/append-no-blocks.conf b/src/test/fixtures/outputs/append-no-blocks.conf
index 11eeb7fe..187bd2c8 100644
--- a/src/test/fixtures/outputs/append-no-blocks.conf
+++ b/src/test/fixtures/outputs/append-no-blocks.conf
@@ -5,7 +5,14 @@ Host test2
 
 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--foo-bar--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio foo-bar
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=jetbrains foo-bar
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--foo-bar--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=disable foo-bar
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/fixtures/outputs/append-no-newline.conf b/src/test/fixtures/outputs/append-no-newline.conf
index 3dad453d..d7e52efa 100644
--- a/src/test/fixtures/outputs/append-no-newline.conf
+++ b/src/test/fixtures/outputs/append-no-newline.conf
@@ -4,7 +4,14 @@ Host test2
   Port 443
 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--foo-bar--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio foo-bar
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=jetbrains foo-bar
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--foo-bar--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=disable foo-bar
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/fixtures/outputs/append-no-related-blocks.conf b/src/test/fixtures/outputs/append-no-related-blocks.conf
index 9b0b4c84..b90a9221 100644
--- a/src/test/fixtures/outputs/append-no-related-blocks.conf
+++ b/src/test/fixtures/outputs/append-no-related-blocks.conf
@@ -11,7 +11,14 @@ some jetbrains config
 
 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--foo-bar--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio foo-bar
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=jetbrains foo-bar
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--foo-bar--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=disable foo-bar
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/fixtures/outputs/disable-autostart.conf b/src/test/fixtures/outputs/disable-autostart.conf
index a22e34d1..9bce080b 100644
--- a/src/test/fixtures/outputs/disable-autostart.conf
+++ b/src/test/fixtures/outputs/disable-autostart.conf
@@ -1,6 +1,13 @@
 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--foo--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --disable-autostart foo
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --disable-autostart --usage-app=jetbrains foo
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--foo--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --disable-autostart --usage-app=disable foo
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/fixtures/outputs/extra-config.conf b/src/test/fixtures/outputs/extra-config.conf
index 5dcff2c8..3186b8d7 100644
--- a/src/test/fixtures/outputs/extra-config.conf
+++ b/src/test/fixtures/outputs/extra-config.conf
@@ -1,6 +1,15 @@
 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--extra--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio extra
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=jetbrains extra
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+  ServerAliveInterval 5
+  ServerAliveCountMax 3
+Host coder-jetbrains--extra--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=disable extra
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/fixtures/outputs/header-command-windows.conf b/src/test/fixtures/outputs/header-command-windows.conf
index 4711c2ab..d14340e4 100644
--- a/src/test/fixtures/outputs/header-command-windows.conf
+++ b/src/test/fixtures/outputs/header-command-windows.conf
@@ -1,6 +1,13 @@
 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--header--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config --header-command "\"C:\Program Files\My Header Command\HeaderCommand.exe\" --url=\"%%CODER_URL%%\" --test=\"foo bar\"" ssh --stdio header
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config --header-command "\"C:\Program Files\My Header Command\HeaderCommand.exe\" --url=\"%%CODER_URL%%\" --test=\"foo bar\"" ssh --stdio --usage-app=jetbrains header
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--header--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config --header-command "\"C:\Program Files\My Header Command\HeaderCommand.exe\" --url=\"%%CODER_URL%%\" --test=\"foo bar\"" ssh --stdio --usage-app=disable header
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/fixtures/outputs/header-command.conf b/src/test/fixtures/outputs/header-command.conf
index 04e422fb..b82f4cf0 100644
--- a/src/test/fixtures/outputs/header-command.conf
+++ b/src/test/fixtures/outputs/header-command.conf
@@ -1,6 +1,13 @@
 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--header--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config --header-command 'my-header-command --url="$CODER_URL" --test="foo bar" --literal='\''$CODER_URL'\''' ssh --stdio header
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config --header-command 'my-header-command --url="$CODER_URL" --test="foo bar" --literal='\''$CODER_URL'\''' ssh --stdio --usage-app=jetbrains header
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--header--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config --header-command 'my-header-command --url="$CODER_URL" --test="foo bar" --literal='\''$CODER_URL'\''' ssh --stdio --usage-app=disable header
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/fixtures/outputs/multiple-workspaces.conf b/src/test/fixtures/outputs/multiple-workspaces.conf
index 8cb3d81b..c6c733e1 100644
--- a/src/test/fixtures/outputs/multiple-workspaces.conf
+++ b/src/test/fixtures/outputs/multiple-workspaces.conf
@@ -1,13 +1,27 @@
 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--foo--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio foo
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=jetbrains foo
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--foo--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=disable foo
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
   LogLevel ERROR
   SetEnv CODER_SSH_SESSION_TYPE=JetBrains
 Host coder-jetbrains--bar--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio bar
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=jetbrains bar
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--bar--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=disable bar
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/fixtures/outputs/no-disable-autostart.conf b/src/test/fixtures/outputs/no-disable-autostart.conf
index 217d332d..5665634d 100644
--- a/src/test/fixtures/outputs/no-disable-autostart.conf
+++ b/src/test/fixtures/outputs/no-disable-autostart.conf
@@ -1,6 +1,13 @@
 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--foo--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio foo
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=jetbrains foo
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--foo--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=disable foo
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/fixtures/outputs/report-usage.conf b/src/test/fixtures/outputs/no-report-usage.conf
similarity index 53%
rename from src/test/fixtures/outputs/report-usage.conf
rename to src/test/fixtures/outputs/no-report-usage.conf
index 635e48ef..27e2ecf1 100644
--- a/src/test/fixtures/outputs/report-usage.conf
+++ b/src/test/fixtures/outputs/no-report-usage.conf
@@ -1,6 +1,13 @@
 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--foo--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=jetbrains foo
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio foo
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--foo--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio foo
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/fixtures/outputs/replace-end-no-newline.conf b/src/test/fixtures/outputs/replace-end-no-newline.conf
index a2977f21..e6a43a9d 100644
--- a/src/test/fixtures/outputs/replace-end-no-newline.conf
+++ b/src/test/fixtures/outputs/replace-end-no-newline.conf
@@ -3,7 +3,14 @@ Host test
 Host test2
   Port 443 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--foo-bar--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio foo-bar
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=jetbrains foo-bar
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--foo-bar--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=disable foo-bar
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/fixtures/outputs/replace-end.conf b/src/test/fixtures/outputs/replace-end.conf
index 3dad453d..d7e52efa 100644
--- a/src/test/fixtures/outputs/replace-end.conf
+++ b/src/test/fixtures/outputs/replace-end.conf
@@ -4,7 +4,14 @@ Host test2
   Port 443
 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--foo-bar--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio foo-bar
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=jetbrains foo-bar
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--foo-bar--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=disable foo-bar
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/fixtures/outputs/replace-middle-ignore-unrelated.conf b/src/test/fixtures/outputs/replace-middle-ignore-unrelated.conf
index 37f73c47..156c95c7 100644
--- a/src/test/fixtures/outputs/replace-middle-ignore-unrelated.conf
+++ b/src/test/fixtures/outputs/replace-middle-ignore-unrelated.conf
@@ -5,7 +5,14 @@ some coder config
 # ------------END-CODER------------
 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--foo-bar--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio foo-bar
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=jetbrains foo-bar
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--foo-bar--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=disable foo-bar
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/fixtures/outputs/replace-middle.conf b/src/test/fixtures/outputs/replace-middle.conf
index 7677238c..803e8823 100644
--- a/src/test/fixtures/outputs/replace-middle.conf
+++ b/src/test/fixtures/outputs/replace-middle.conf
@@ -2,7 +2,14 @@ Host test
   Port 80
 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--foo-bar--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio foo-bar
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=jetbrains foo-bar
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--foo-bar--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=disable foo-bar
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/fixtures/outputs/replace-only.conf b/src/test/fixtures/outputs/replace-only.conf
index 566a8522..d04a5c6c 100644
--- a/src/test/fixtures/outputs/replace-only.conf
+++ b/src/test/fixtures/outputs/replace-only.conf
@@ -1,6 +1,13 @@
 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--foo-bar--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio foo-bar
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=jetbrains foo-bar
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--foo-bar--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=disable foo-bar
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/fixtures/outputs/replace-start.conf b/src/test/fixtures/outputs/replace-start.conf
index 04cbe274..d13ff038 100644
--- a/src/test/fixtures/outputs/replace-start.conf
+++ b/src/test/fixtures/outputs/replace-start.conf
@@ -1,6 +1,13 @@
 # --- START CODER JETBRAINS test.coder.invalid
 Host coder-jetbrains--foo-bar--test.coder.invalid
-  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio foo-bar
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=jetbrains foo-bar
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+Host coder-jetbrains--foo-bar--test.coder.invalid--bg
+  ProxyCommand /tmp/coder-gateway/test.coder.invalid/coder-linux-amd64 --global-config /tmp/coder-gateway/test.coder.invalid/config ssh --stdio --usage-app=disable foo-bar
   ConnectTimeout 0
   StrictHostKeyChecking no
   UserKnownHostsFile /dev/null
diff --git a/src/test/kotlin/com/coder/gateway/cli/CoderCLIManagerTest.kt b/src/test/kotlin/com/coder/gateway/cli/CoderCLIManagerTest.kt
index 51a6339a..428f04da 100644
--- a/src/test/kotlin/com/coder/gateway/cli/CoderCLIManagerTest.kt
+++ b/src/test/kotlin/com/coder/gateway/cli/CoderCLIManagerTest.kt
@@ -313,19 +313,19 @@ internal class CoderCLIManagerTest {
             ).joinToString(System.lineSeparator())
         val tests =
             listOf(
-                SSHTest(listOf("foo", "bar"), null, "multiple-workspaces", "blank"),
-                SSHTest(listOf("foo", "bar"), null, "multiple-workspaces", "blank"),
-                SSHTest(listOf("foo-bar"), "blank", "append-blank", "blank"),
-                SSHTest(listOf("foo-bar"), "blank-newlines", "append-blank-newlines", "blank"),
-                SSHTest(listOf("foo-bar"), "existing-end", "replace-end", "no-blocks"),
-                SSHTest(listOf("foo-bar"), "existing-end-no-newline", "replace-end-no-newline", "no-blocks"),
-                SSHTest(listOf("foo-bar"), "existing-middle", "replace-middle", "no-blocks"),
-                SSHTest(listOf("foo-bar"), "existing-middle-and-unrelated", "replace-middle-ignore-unrelated", "no-related-blocks"),
-                SSHTest(listOf("foo-bar"), "existing-only", "replace-only", "blank"),
-                SSHTest(listOf("foo-bar"), "existing-start", "replace-start", "no-blocks"),
-                SSHTest(listOf("foo-bar"), "no-blocks", "append-no-blocks", "no-blocks"),
-                SSHTest(listOf("foo-bar"), "no-related-blocks", "append-no-related-blocks", "no-related-blocks"),
-                SSHTest(listOf("foo-bar"), "no-newline", "append-no-newline", "no-blocks"),
+                SSHTest(listOf("foo", "bar"), null, "multiple-workspaces", "blank", features = Features(false, true)),
+                SSHTest(listOf("foo", "bar"), null, "multiple-workspaces", "blank", features = Features(false, true)),
+                SSHTest(listOf("foo-bar"), "blank", "append-blank", "blank", features = Features(false, true)),
+                SSHTest(listOf("foo-bar"), "blank-newlines", "append-blank-newlines", "blank", features = Features(false, true)),
+                SSHTest(listOf("foo-bar"), "existing-end", "replace-end", "no-blocks", features = Features(false, true)),
+                SSHTest(listOf("foo-bar"), "existing-end-no-newline", "replace-end-no-newline", "no-blocks", features = Features(false, true)),
+                SSHTest(listOf("foo-bar"), "existing-middle", "replace-middle", "no-blocks", features = Features(false, true)),
+                SSHTest(listOf("foo-bar"), "existing-middle-and-unrelated", "replace-middle-ignore-unrelated", "no-related-blocks", features = Features(false, true)),
+                SSHTest(listOf("foo-bar"), "existing-only", "replace-only", "blank", features = Features(false, true)),
+                SSHTest(listOf("foo-bar"), "existing-start", "replace-start", "no-blocks", features = Features(false, true)),
+                SSHTest(listOf("foo-bar"), "no-blocks", "append-no-blocks", "no-blocks", features = Features(false, true)),
+                SSHTest(listOf("foo-bar"), "no-related-blocks", "append-no-related-blocks", "no-related-blocks", features = Features(false, true)),
+                SSHTest(listOf("foo-bar"), "no-newline", "append-no-newline", "no-blocks", features = Features(false, true)),
                 if (getOS() == OS.WINDOWS) {
                     SSHTest(
                         listOf("header"),
@@ -333,6 +333,7 @@ internal class CoderCLIManagerTest {
                         "header-command-windows",
                         "blank",
                         """"C:\Program Files\My Header Command\HeaderCommand.exe" --url="%CODER_URL%" --test="foo bar"""",
+                        features = Features(false, true)
                     )
                 } else {
                     SSHTest(
@@ -341,17 +342,19 @@ internal class CoderCLIManagerTest {
                         "header-command",
                         "blank",
                         "my-header-command --url=\"\$CODER_URL\" --test=\"foo bar\" --literal='\$CODER_URL'",
+                        features = Features(false, true)
                     )
                 },
-                SSHTest(listOf("foo"), null, "disable-autostart", "blank", "", true, Features(true)),
-                SSHTest(listOf("foo"), null, "no-disable-autostart", "blank", "", true, Features(false)),
-                SSHTest(listOf("foo"), null, "report-usage", "blank", "", true, Features(false, true)),
+                SSHTest(listOf("foo"), null, "disable-autostart", "blank", "", true, Features(true, true)),
+                SSHTest(listOf("foo"), null, "no-disable-autostart", "blank", "", true, Features(false, true)),
+                SSHTest(listOf("foo"), null, "no-report-usage", "blank", "", true, Features(false, false)),
                 SSHTest(
                     listOf("extra"),
                     null,
                     "extra-config",
                     "blank",
                     extraConfig = extraConfig,
+                    features = Features(false, true)
                 ),
                 SSHTest(
                     listOf("extra"),
@@ -359,6 +362,7 @@ internal class CoderCLIManagerTest {
                     "extra-config",
                     "blank",
                     env = Environment(mapOf(CODER_SSH_CONFIG_OPTIONS to extraConfig)),
+                    features = Features(false, true)
                 ),
             )