diff --git a/CHANGELOG.md b/CHANGELOG.md
index b3428209..dff09f10 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,12 @@
 
 ## Unreleased
 
+### Changed
+
+- Disable autostarting workspaces by default on macOS to prevent an issue where
+  it wakes periodically and keeps the workspace on.  This can be toggled via the
+  "Disable autostart" setting.
+
 ## 2.9.3 - 2024-02-10
 
 ### Fixed
diff --git a/src/main/kotlin/com/coder/gateway/CoderSettingsConfigurable.kt b/src/main/kotlin/com/coder/gateway/CoderSettingsConfigurable.kt
index 73aaff1f..70ffb85c 100644
--- a/src/main/kotlin/com/coder/gateway/CoderSettingsConfigurable.kt
+++ b/src/main/kotlin/com/coder/gateway/CoderSettingsConfigurable.kt
@@ -1,8 +1,8 @@
 package com.coder.gateway
 
 import com.coder.gateway.services.CoderSettingsService
-import com.coder.gateway.util.canCreateDirectory
 import com.coder.gateway.services.CoderSettingsState
+import com.coder.gateway.util.canCreateDirectory
 import com.intellij.openapi.components.service
 import com.intellij.openapi.options.BoundConfigurable
 import com.intellij.openapi.ui.DialogPanel
@@ -102,6 +102,13 @@ class CoderSettingsConfigurable : BoundConfigurable("Coder") {
                         CoderGatewayBundle.message("gateway.connector.settings.tls-alt-name.comment")
                     )
             }.layout(RowLayout.PARENT_GRID)
+            row(CoderGatewayBundle.message("gateway.connector.settings.disable-autostart.heading")) {
+                checkBox(CoderGatewayBundle.message("gateway.connector.settings.disable-autostart.title"))
+                    .bindSelected(state::disableAutostart)
+                    .comment(
+                        CoderGatewayBundle.message("gateway.connector.settings.disable-autostart.comment")
+                    )
+            }.layout(RowLayout.PARENT_GRID)
         }
     }
 
diff --git a/src/main/kotlin/com/coder/gateway/cli/CoderCLIManager.kt b/src/main/kotlin/com/coder/gateway/cli/CoderCLIManager.kt
index 689fcd11..89b409aa 100644
--- a/src/main/kotlin/com/coder/gateway/cli/CoderCLIManager.kt
+++ b/src/main/kotlin/com/coder/gateway/cli/CoderCLIManager.kt
@@ -96,6 +96,13 @@ fun ensureCLI(
     return if (cliMatches == null && dataCLIMatches != null) dataCLI else cli
 }
 
+/**
+ * The supported features of the CLI.
+ */
+data class Features (
+    val disableAutostart: Boolean = false,
+)
+
 /**
  * Manage the CLI for a single deployment.
  */
@@ -199,9 +206,11 @@ class CoderCLIManager(
 
     /**
      * Configure SSH to use this binary.
+     *
+     * This can take supported features for testing purposes only.
      */
-    fun configSsh(workspaceNames: List<String>) {
-        writeSSHConfig(modifySSHConfig(readSSHConfig(), workspaceNames))
+    fun configSsh(workspaceNames: List<String>, feats: Features = features) {
+        writeSSHConfig(modifySSHConfig(readSSHConfig(), workspaceNames, feats))
     }
 
     /**
@@ -219,8 +228,11 @@ class CoderCLIManager(
      * Given an existing SSH config modify it to add or remove the config for
      * this deployment and return the modified config or null if it does not
      * need to be modified.
+     *
+     * If features are not provided, calculate them based on the binary
+     * version.
      */
-    private fun modifySSHConfig(contents: String?, workspaceNames: List<String>): String? {
+    private fun modifySSHConfig(contents: String?, workspaceNames: List<String>, feats: Features): String? {
         val host = deploymentURL.safeHost()
         val startBlock = "# --- START CODER JETBRAINS $host"
         val endBlock = "# --- END CODER JETBRAINS $host"
@@ -230,7 +242,8 @@ class CoderCLIManager(
             "--global-config", escape(coderConfigPath.toString()),
             if (settings.headerCommand.isNotBlank()) "--header-command" else null,
             if (settings.headerCommand.isNotBlank()) escapeSubcommand(settings.headerCommand) else null,
-           "ssh", "--stdio")
+           "ssh", "--stdio",
+            if (settings.disableAutostart && feats.disableAutostart) "--disable-autostart" else null)
         val blockContent = workspaceNames.joinToString(
             System.lineSeparator(),
             startBlock + System.lineSeparator(),
@@ -238,7 +251,7 @@ class CoderCLIManager(
             transform = {
                 """
                 Host ${getHostName(deploymentURL, it)}
-                  ProxyCommand ${proxyArgs.joinToString(" ")} ${it}
+                  ProxyCommand ${proxyArgs.joinToString(" ")} $it
                   ConnectTimeout 0
                   StrictHostKeyChecking no
                   UserKnownHostsFile /dev/null
@@ -333,31 +346,36 @@ class CoderCLIManager(
     }
 
     /**
-     * Returns true if the CLI has the same major/minor/patch version as the
-     * provided version, false if it does not match, or null if the CLI version
-     * could not be determined because the binary could not be executed or the
-     * version could not be parsed.
+     * Like version(), but logs errors instead of throwing them.
      */
-    fun matchesVersion(rawBuildVersion: String): Boolean? {
-        val cliVersion = try {
+    private fun tryVersion(): SemVer? {
+        return try {
             version()
         } catch (e: Exception) {
             when (e) {
                 is JsonSyntaxException,
                 is InvalidVersionException -> {
                     logger.info("Got invalid version from $localBinaryPath: ${e.message}")
-                    return null
                 }
                 else -> {
                     // An error here most likely means the CLI does not exist or
                     // it executed successfully but output no version which
                     // suggests it is not the right binary.
                     logger.info("Unable to determine $localBinaryPath version: ${e.message}")
-                    return null
                 }
             }
+            null
         }
+    }
 
+    /**
+     * Returns true if the CLI has the same major/minor/patch version as the
+     * provided version, false if it does not match, or null if the CLI version
+     * could not be determined because the binary could not be executed or the
+     * version could not be parsed.
+     */
+    fun matchesVersion(rawBuildVersion: String): Boolean? {
+        val cliVersion = tryVersion() ?: return null
         val buildVersion = try {
             SemVer.parse(rawBuildVersion)
         } catch (e: InvalidVersionException) {
@@ -383,6 +401,18 @@ class CoderCLIManager(
         return stdout
     }
 
+    val features: Features
+        get() {
+            val version = tryVersion()
+            return if (version == null) {
+                Features()
+            } else {
+                Features(
+                    // Autostart with SSH was added in 2.5.0.
+                    disableAutostart = version >= SemVer(2, 5, 0))
+            }
+        }
+
     companion object {
         val logger = Logger.getInstance(CoderCLIManager::class.java.simpleName)
 
diff --git a/src/main/kotlin/com/coder/gateway/services/CoderSettingsState.kt b/src/main/kotlin/com/coder/gateway/services/CoderSettingsState.kt
index da7fcb3e..28081297 100644
--- a/src/main/kotlin/com/coder/gateway/services/CoderSettingsState.kt
+++ b/src/main/kotlin/com/coder/gateway/services/CoderSettingsState.kt
@@ -1,5 +1,7 @@
 package com.coder.gateway.services
 
+import com.coder.gateway.util.OS
+import com.coder.gateway.util.getOS
 import com.intellij.openapi.components.PersistentStateComponent
 import com.intellij.openapi.components.RoamingType
 import com.intellij.openapi.components.Service
@@ -56,6 +58,10 @@ class CoderSettingsState(
     // connections. This is useful when the hostname used to connect to the
     // Coder service does not match the hostname in the TLS certificate.
     var tlsAlternateHostname: String = "",
+    // Whether to add --disable-autostart to the proxy command.  This works
+    // around issues on macOS where it periodically wakes and Gateway
+    // reconnects, keeping the workspace constantly up.
+    var disableAutostart: Boolean = getOS() == OS.MAC,
 ) : PersistentStateComponent<CoderSettingsState> {
     override fun getState(): CoderSettingsState {
         return this
diff --git a/src/main/kotlin/com/coder/gateway/settings/CoderSettings.kt b/src/main/kotlin/com/coder/gateway/settings/CoderSettings.kt
index d2904c2c..f0050191 100644
--- a/src/main/kotlin/com/coder/gateway/settings/CoderSettings.kt
+++ b/src/main/kotlin/com/coder/gateway/settings/CoderSettings.kt
@@ -35,6 +35,9 @@ open class CoderSettings(
     val headerCommand: String
         get() = state.headerCommand
 
+    val disableAutostart: Boolean
+        get() = state.disableAutostart
+
     /**
      * Where the specified deployment should put its data.
      */
diff --git a/src/main/resources/messages/CoderGatewayBundle.properties b/src/main/resources/messages/CoderGatewayBundle.properties
index 1dac9df4..4b1a334f 100644
--- a/src/main/resources/messages/CoderGatewayBundle.properties
+++ b/src/main/resources/messages/CoderGatewayBundle.properties
@@ -111,3 +111,9 @@ gateway.connector.settings.tls-alt-name.comment=Optionally set this to \
   an alternate hostname used for verifying TLS connections. This is useful \
   when the hostname used to connect to the Coder service does not match the \
   hostname in the TLS certificate.
+gateway.connector.settings.disable-autostart.heading=Autostart:
+gateway.connector.settings.disable-autostart.title=Disable autostart
+gateway.connector.settings.disable-autostart.comment=Checking this box will \
+  cause the plugin to configure the CLI with --disable-autostart. You must go \
+  through the IDE selection again for the plugin to reconfigure the CLI with \
+  this setting.
diff --git a/src/test/fixtures/outputs/disable-autostart.conf b/src/test/fixtures/outputs/disable-autostart.conf
new file mode 100644
index 00000000..a22e34d1
--- /dev/null
+++ b/src/test/fixtures/outputs/disable-autostart.conf
@@ -0,0 +1,9 @@
+# --- 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
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+# --- END CODER JETBRAINS test.coder.invalid
diff --git a/src/test/fixtures/outputs/no-disable-autostart.conf b/src/test/fixtures/outputs/no-disable-autostart.conf
new file mode 100644
index 00000000..217d332d
--- /dev/null
+++ b/src/test/fixtures/outputs/no-disable-autostart.conf
@@ -0,0 +1,9 @@
+# --- 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
+  ConnectTimeout 0
+  StrictHostKeyChecking no
+  UserKnownHostsFile /dev/null
+  LogLevel ERROR
+  SetEnv CODER_SSH_SESSION_TYPE=JetBrains
+# --- END CODER JETBRAINS test.coder.invalid
diff --git a/src/test/kotlin/com/coder/gateway/cli/CoderCLIManagerTest.kt b/src/test/kotlin/com/coder/gateway/cli/CoderCLIManagerTest.kt
index 3c7383b4..1b1a29f5 100644
--- a/src/test/kotlin/com/coder/gateway/cli/CoderCLIManagerTest.kt
+++ b/src/test/kotlin/com/coder/gateway/cli/CoderCLIManagerTest.kt
@@ -33,18 +33,18 @@ import kotlin.test.assertTrue
 
 internal class CoderCLIManagerTest {
     private fun mkbin(version: String): String {
-        return listOf("#!/bin/sh", """echo '{"version": "${version}"}'""")
+        return listOf("#!/bin/sh", """echo '{"version": "$version"}'""")
             .joinToString("\n")
     }
 
-    private fun mockServer(errorCode: Int = 0): Pair<HttpServer, URL> {
+    private fun mockServer(errorCode: Int = 0, version: String? = null): Pair<HttpServer, URL> {
         val srv = HttpServer.create(InetSocketAddress(0), 0)
         srv.createContext("/") {exchange ->
             var code = HttpURLConnection.HTTP_OK
             // TODO: Is there some simple way to create an executable file on
             // Windows without having to execute something to generate said
             // executable or having to commit one to the repo?
-            var response = mkbin("${srv.address.port}.0.0")
+            var response = mkbin(version ?: "${srv.address.port}.0.0")
             val eTags = exchange.requestHeaders["If-None-Match"]
             if (exchange.requestURI.path == "/bin/override") {
                 code = HttpURLConnection.HTTP_OK
@@ -234,7 +234,15 @@ internal class CoderCLIManagerTest {
         srv2.stop(0)
     }
 
-    data class SSHTest(val workspaces: List<String>, val input: String?, val output: String, val remove: String, val headerCommand: String?)
+    data class SSHTest(
+        val workspaces: List<String>,
+        val input: String?,
+        val output: String,
+        val remove: String,
+        val headerCommand: String?,
+        val disableAutostart: Boolean = false,
+        val features: Features? = null,
+    )
 
     @Test
     fun testConfigureSSH() {
@@ -256,13 +264,16 @@ internal class CoderCLIManagerTest {
                 SSHTest(listOf("header"), null, "header-command-windows", "blank", """"C:\Program Files\My Header Command\HeaderCommand.exe" --url="%CODER_URL%" --test="foo bar"""")
             } else {
                 SSHTest(listOf("header"), null, "header-command", "blank", "my-header-command --url=\"\$CODER_URL\" --test=\"foo bar\" --literal='\$CODER_URL'")
-            }
+            },
+            SSHTest(listOf("foo"), null, "disable-autostart", "blank", null, true, Features(true)),
+            SSHTest(listOf("foo"), null, "no-disable-autostart", "blank", null, true, Features(false)),
         )
 
         val newlineRe = "\r?\n".toRegex()
 
         tests.forEach {
             val settings = CoderSettings(CoderSettingsState(
+                disableAutostart = it.disableAutostart,
                 dataDirectory = tmpdir.resolve("configure-ssh").toString(),
                 headerCommand = it.headerCommand ?: ""),
                 sshConfigPath = tmpdir.resolve(it.input + "_to_" + it.output + ".conf"))
@@ -285,12 +296,12 @@ internal class CoderCLIManagerTest {
                 .replace("/tmp/coder-gateway/test.coder.invalid/coder-linux-amd64", escape(ccm.localBinaryPath.toString()))
 
             // Add workspaces.
-            ccm.configSsh(it.workspaces)
+            ccm.configSsh(it.workspaces, it.features ?: Features())
 
             assertEquals(expectedConf, settings.sshConfigPath.toFile().readText())
 
             // Remove configuration.
-            ccm.configSsh(emptyList())
+            ccm.configSsh(emptyList(), it.features ?: Features())
 
             // Remove is the configuration we expect after removing.
             assertEquals(
@@ -540,6 +551,31 @@ internal class CoderCLIManagerTest {
         srv.stop(0)
     }
 
+    @Test
+    fun testFeatures() {
+        if (getOS() == OS.WINDOWS) {
+            return // Cannot execute mock binaries on Windows.
+        }
+
+        val tests = listOf(
+            Pair("2.5.0", Features(true)),
+            Pair("4.9.0", Features(true)),
+            Pair("2.4.9", Features(false)),
+            Pair("1.0.1", Features(false)),
+        )
+
+        tests.forEach {
+            val (srv, url) = mockServer(version = it.first)
+            val ccm = CoderCLIManager(url, CoderSettings(CoderSettingsState(
+                dataDirectory = tmpdir.resolve("features").toString()))
+            )
+            assertEquals(true, ccm.download())
+            assertEquals(it.second, ccm.features, "version: ${it.first}")
+
+            srv.stop(0)
+        }
+    }
+
     companion object {
         private val tmpdir: Path = Path.of(System.getProperty("java.io.tmpdir")).resolve("coder-gateway-test/cli-manager")
 
diff --git a/src/test/kotlin/com/coder/gateway/settings/CoderSettingsTest.kt b/src/test/kotlin/com/coder/gateway/settings/CoderSettingsTest.kt
index 26a121f2..ab1943c6 100644
--- a/src/test/kotlin/com/coder/gateway/settings/CoderSettingsTest.kt
+++ b/src/test/kotlin/com/coder/gateway/settings/CoderSettingsTest.kt
@@ -1,15 +1,14 @@
 package com.coder.gateway.settings
 
 import com.coder.gateway.services.CoderSettingsState
-import kotlin.test.Test
-import kotlin.test.assertContains
-import kotlin.test.assertEquals
-
 import com.coder.gateway.util.OS
 import com.coder.gateway.util.getOS
 import com.coder.gateway.util.withPath
 import java.net.URL
 import java.nio.file.Path
+import kotlin.test.Test
+import kotlin.test.assertContains
+import kotlin.test.assertEquals
 
 internal class CoderSettingsTest {
     @Test
@@ -179,14 +178,15 @@ internal class CoderSettingsTest {
         // Make sure the remaining settings are being conveyed.
         val settings = CoderSettings(
             CoderSettingsState(
-            enableDownloads = false,
-            enableBinaryDirectoryFallback = true,
-            headerCommand = "test header",
-            tlsCertPath = "tls cert path",
-            tlsKeyPath = "tls key path",
-            tlsCAPath = "tls ca path",
-            tlsAlternateHostname = "tls alt hostname",
-        )
+                enableDownloads = false,
+                enableBinaryDirectoryFallback = true,
+                headerCommand = "test header",
+                tlsCertPath = "tls cert path",
+                tlsKeyPath = "tls key path",
+                tlsCAPath = "tls ca path",
+                tlsAlternateHostname = "tls alt hostname",
+                disableAutostart = true,
+            )
         )
 
         assertEquals(false, settings.enableDownloads)
@@ -196,5 +196,6 @@ internal class CoderSettingsTest {
         assertEquals("tls key path", settings.tls.keyPath)
         assertEquals("tls ca path", settings.tls.caPath)
         assertEquals("tls alt hostname", settings.tls.altHostname)
+        assertEquals(true, settings.disableAutostart)
     }
 }

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