diff --git a/CHANGELOG.md b/CHANGELOG.md
index 40ad0740..235d2957 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,7 @@
 ### Added
 
 - application name can now be displayed as the main title page instead of the URL
+- automatic mTLS certificate regeneration and retry mechanism
 
 ### Changed
 
diff --git a/src/main/kotlin/com/coder/toolbox/CoderRemoteProvider.kt b/src/main/kotlin/com/coder/toolbox/CoderRemoteProvider.kt
index 6084880e..217d4b1e 100644
--- a/src/main/kotlin/com/coder/toolbox/CoderRemoteProvider.kt
+++ b/src/main/kotlin/com/coder/toolbox/CoderRemoteProvider.kt
@@ -414,14 +414,14 @@ class CoderRemoteProvider(
      * Auto-login only on first the firs run if there is a url & token configured or the auth
      * should be done via certificates.
      */
-    private fun shouldDoAutoSetup(): Boolean = firstRun && (canAutoLogin() || !settings.requireTokenAuth)
+    private fun shouldDoAutoSetup(): Boolean = firstRun && (canAutoLogin() || !settings.requiresTokenAuth)
 
     fun canAutoLogin(): Boolean = !context.secrets.tokenFor(context.deploymentUrl).isNullOrBlank()
 
     private fun onConnect(client: CoderRestClient, cli: CoderCLIManager) {
         // Store the URL and token for use next time.
         context.settingsStore.updateLastUsedUrl(client.url)
-        if (context.settingsStore.requireTokenAuth) {
+        if (context.settingsStore.requiresTokenAuth) {
             context.secrets.storeTokenFor(client.url, client.token ?: "")
             context.logger.info("Deployment URL and token were stored and will be available for automatic connection")
         } else {
diff --git a/src/main/kotlin/com/coder/toolbox/cli/CoderCLIManager.kt b/src/main/kotlin/com/coder/toolbox/cli/CoderCLIManager.kt
index eb289af6..0fe6c25e 100644
--- a/src/main/kotlin/com/coder/toolbox/cli/CoderCLIManager.kt
+++ b/src/main/kotlin/com/coder/toolbox/cli/CoderCLIManager.kt
@@ -19,6 +19,7 @@ import com.coder.toolbox.sdk.v2.models.Workspace
 import com.coder.toolbox.sdk.v2.models.WorkspaceAgent
 import com.coder.toolbox.settings.SignatureFallbackStrategy.ALLOW
 import com.coder.toolbox.util.InvalidVersionException
+import com.coder.toolbox.util.ReloadableTlsContext
 import com.coder.toolbox.util.SemVer
 import com.coder.toolbox.util.escape
 import com.coder.toolbox.util.escapeSubcommand
@@ -153,7 +154,8 @@ class CoderCLIManager(
         }
         val okHttpClient = CoderHttpClientBuilder.build(
             context,
-            interceptors
+            interceptors,
+            ReloadableTlsContext(context.settingsStore.readOnly().tls)
         )
 
         val retrofit = Retrofit.Builder()
diff --git a/src/main/kotlin/com/coder/toolbox/sdk/CoderHttpClientBuilder.kt b/src/main/kotlin/com/coder/toolbox/sdk/CoderHttpClientBuilder.kt
index 86474d9c..a526db05 100644
--- a/src/main/kotlin/com/coder/toolbox/sdk/CoderHttpClientBuilder.kt
+++ b/src/main/kotlin/com/coder/toolbox/sdk/CoderHttpClientBuilder.kt
@@ -2,24 +2,19 @@ package com.coder.toolbox.sdk
 
 import com.coder.toolbox.CoderToolboxContext
 import com.coder.toolbox.util.CoderHostnameVerifier
-import com.coder.toolbox.util.coderSocketFactory
-import com.coder.toolbox.util.coderTrustManagers
+import com.coder.toolbox.util.ReloadableTlsContext
 import com.jetbrains.toolbox.api.remoteDev.connection.ProxyAuth
 import okhttp3.Credentials
 import okhttp3.Interceptor
 import okhttp3.OkHttpClient
-import javax.net.ssl.X509TrustManager
 
 object CoderHttpClientBuilder {
     fun build(
         context: CoderToolboxContext,
-        interceptors: List<Interceptor>
+        interceptors: List<Interceptor>,
+        tlsContext: ReloadableTlsContext
     ): OkHttpClient {
-        val settings = context.settingsStore.readOnly()
-
-        val socketFactory = coderSocketFactory(settings.tls)
-        val trustManagers = coderTrustManagers(settings.tls.caPath)
-        var builder = OkHttpClient.Builder()
+        val builder = OkHttpClient.Builder()
 
         context.proxySettings.getProxy()?.let { proxy ->
             context.logger.info("proxy: $proxy")
@@ -43,8 +38,8 @@ object CoderHttpClientBuilder {
                 .build()
         }
 
-        builder.sslSocketFactory(socketFactory, trustManagers[0] as X509TrustManager)
-            .hostnameVerifier(CoderHostnameVerifier(settings.tls.altHostname))
+        builder.sslSocketFactory(tlsContext.sslSocketFactory, tlsContext.trustManager)
+            .hostnameVerifier(CoderHostnameVerifier(context.settingsStore.tls.altHostname))
             .retryOnConnectionFailure(true)
 
         interceptors.forEach { interceptor ->
diff --git a/src/main/kotlin/com/coder/toolbox/sdk/CoderRestClient.kt b/src/main/kotlin/com/coder/toolbox/sdk/CoderRestClient.kt
index 7023c764..b44352d3 100644
--- a/src/main/kotlin/com/coder/toolbox/sdk/CoderRestClient.kt
+++ b/src/main/kotlin/com/coder/toolbox/sdk/CoderRestClient.kt
@@ -7,6 +7,7 @@ import com.coder.toolbox.sdk.convertors.LoggingConverterFactory
 import com.coder.toolbox.sdk.convertors.OSConverter
 import com.coder.toolbox.sdk.convertors.UUIDConverter
 import com.coder.toolbox.sdk.ex.APIResponseException
+import com.coder.toolbox.sdk.interceptors.CertificateRefreshInterceptor
 import com.coder.toolbox.sdk.interceptors.Interceptors
 import com.coder.toolbox.sdk.v2.CoderV2RestFacade
 import com.coder.toolbox.sdk.v2.models.ApiErrorResponse
@@ -20,6 +21,7 @@ import com.coder.toolbox.sdk.v2.models.WorkspaceBuild
 import com.coder.toolbox.sdk.v2.models.WorkspaceBuildReason
 import com.coder.toolbox.sdk.v2.models.WorkspaceResource
 import com.coder.toolbox.sdk.v2.models.WorkspaceTransition
+import com.coder.toolbox.util.ReloadableTlsContext
 import com.squareup.moshi.Moshi
 import okhttp3.OkHttpClient
 import retrofit2.Response
@@ -40,6 +42,7 @@ open class CoderRestClient(
     val token: String?,
     private val pluginVersion: String = "development",
 ) {
+    private lateinit var tlsContext: ReloadableTlsContext
     private lateinit var moshi: Moshi
     private lateinit var httpClient: OkHttpClient
     private lateinit var retroRestClient: CoderV2RestFacade
@@ -60,12 +63,17 @@ open class CoderRestClient(
                 .add(OSConverter())
                 .add(UUIDConverter())
                 .build()
+
+        tlsContext = ReloadableTlsContext(context.settingsStore.readOnly().tls)
+
         val interceptors = buildList {
-            if (context.settingsStore.requireTokenAuth) {
+            if (context.settingsStore.requiresTokenAuth) {
                 if (token.isNullOrBlank()) {
                     throw IllegalStateException("Token is required for $url deployment")
                 }
                 add(Interceptors.tokenAuth(token))
+            } else if (context.settingsStore.requiresMTlsAuth && context.settingsStore.tls.certRefreshCommand?.isNotBlank() == true) {
+                add(CertificateRefreshInterceptor(context, tlsContext))
             }
             add((Interceptors.userAgent(pluginVersion)))
             add(Interceptors.externalHeaders(context, url))
@@ -74,7 +82,8 @@ open class CoderRestClient(
 
         httpClient = CoderHttpClientBuilder.build(
             context,
-            interceptors
+            interceptors,
+            tlsContext
         )
 
         retroRestClient =
diff --git a/src/main/kotlin/com/coder/toolbox/sdk/interceptors/CertificateRefreshInterceptor.kt b/src/main/kotlin/com/coder/toolbox/sdk/interceptors/CertificateRefreshInterceptor.kt
new file mode 100644
index 00000000..55dae436
--- /dev/null
+++ b/src/main/kotlin/com/coder/toolbox/sdk/interceptors/CertificateRefreshInterceptor.kt
@@ -0,0 +1,53 @@
+package com.coder.toolbox.sdk.interceptors
+
+import com.coder.toolbox.CoderToolboxContext
+import com.coder.toolbox.util.ReloadableTlsContext
+import okhttp3.Interceptor
+import okhttp3.Response
+import org.zeroturnaround.exec.ProcessExecutor
+import javax.net.ssl.SSLHandshakeException
+import javax.net.ssl.SSLPeerUnverifiedException
+
+class CertificateRefreshInterceptor(
+    private val context: CoderToolboxContext,
+    private val tlsContext: ReloadableTlsContext
+) : Interceptor {
+    override fun intercept(chain: Interceptor.Chain): Response {
+        val request = chain.request()
+        try {
+            return chain.proceed(request)
+        } catch (e: Exception) {
+            if ((e is SSLHandshakeException || e is SSLPeerUnverifiedException) && (e.message?.contains("certificate_expired") == true)) {
+                val command = context.settingsStore.tls.certRefreshCommand
+                if (command.isNullOrBlank()) {
+                    throw IllegalStateException(
+                        "Certificate expiration interceptor was set but the refresh command was removed in the meantime",
+                        e
+                    )
+                }
+
+                context.logger.info("SSL handshake exception encountered: certificates expired. Running certificate refresh command: $command")
+                try {
+                    val result = ProcessExecutor()
+                        .command(command.split(" ").toList())
+                        .exitValueNormal()
+                        .readOutput(true)
+                        .execute()
+                    context.logger.info("`$command`: ${result.outputUTF8()}")
+
+                    if (result.exitValue == 0) {
+                        context.logger.info("Certificate refresh command executed successfully. Reloading SSL certificates.")
+                        tlsContext.reload()
+                        // Retry the request
+                        return chain.proceed(request)
+                    } else {
+                        context.logger.error("Certificate refresh command failed with exit code ${result.exitValue}")
+                    }
+                } catch (ex: Exception) {
+                    context.logger.error(ex, "Failed to execute certificate refresh command")
+                }
+            }
+            throw e
+        }
+    }
+}
diff --git a/src/main/kotlin/com/coder/toolbox/settings/ReadOnlyCoderSettings.kt b/src/main/kotlin/com/coder/toolbox/settings/ReadOnlyCoderSettings.kt
index edf4801f..689f2793 100644
--- a/src/main/kotlin/com/coder/toolbox/settings/ReadOnlyCoderSettings.kt
+++ b/src/main/kotlin/com/coder/toolbox/settings/ReadOnlyCoderSettings.kt
@@ -114,7 +114,12 @@ interface ReadOnlyCoderSettings {
     /**
      * Whether login should be done with a token
      */
-    val requireTokenAuth: Boolean
+    val requiresTokenAuth: Boolean
+
+    /**
+     * Whether the authentication is done with certificates.
+     */
+    val requiresMTlsAuth: Boolean
 
     /**
      * Whether to add --disable-autostart to the proxy command.  This works
@@ -216,6 +221,12 @@ interface ReadOnlyTLSSettings {
      * Coder service does not match the hostname in the TLS certificate.
      */
     val altHostname: String?
+
+    /**
+     * Command to run when certificates expire and SSLHandshakeException
+     * is raised with `Received fatal alert: certificate_expired` as message
+     */
+    val certRefreshCommand: String?
 }
 
 enum class SignatureFallbackStrategy {
diff --git a/src/main/kotlin/com/coder/toolbox/store/CoderSettingsStore.kt b/src/main/kotlin/com/coder/toolbox/store/CoderSettingsStore.kt
index ed8f009c..ab8e54be 100644
--- a/src/main/kotlin/com/coder/toolbox/store/CoderSettingsStore.kt
+++ b/src/main/kotlin/com/coder/toolbox/store/CoderSettingsStore.kt
@@ -32,7 +32,8 @@ class CoderSettingsStore(
         override val certPath: String?,
         override val keyPath: String?,
         override val caPath: String?,
-        override val altHostname: String?
+        override val altHostname: String?,
+        override val certRefreshCommand: String?
     ) : ReadOnlyTLSSettings
 
     // Properties implementation
@@ -62,9 +63,11 @@ class CoderSettingsStore(
             certPath = store[TLS_CERT_PATH],
             keyPath = store[TLS_KEY_PATH],
             caPath = store[TLS_CA_PATH],
-            altHostname = store[TLS_ALTERNATE_HOSTNAME]
+            altHostname = store[TLS_ALTERNATE_HOSTNAME],
+            certRefreshCommand = store[TLS_CERT_REFRESH_COMMAND]
         )
-    override val requireTokenAuth: Boolean get() = tls.certPath.isNullOrBlank() || tls.keyPath.isNullOrBlank()
+    override val requiresTokenAuth: Boolean get() = tls.certPath.isNullOrBlank() || tls.keyPath.isNullOrBlank()
+    override val requiresMTlsAuth: Boolean get() = tls.certPath?.isNotBlank() == true && tls.keyPath?.isNotBlank() == true
     override val disableAutostart: Boolean
         get() = store[DISABLE_AUTOSTART]?.toBooleanStrictOrNull() ?: (getOS() == OS.MAC)
     override val isSshWildcardConfigEnabled: Boolean
diff --git a/src/main/kotlin/com/coder/toolbox/store/StoreKeys.kt b/src/main/kotlin/com/coder/toolbox/store/StoreKeys.kt
index bc46c4fd..c199aecd 100644
--- a/src/main/kotlin/com/coder/toolbox/store/StoreKeys.kt
+++ b/src/main/kotlin/com/coder/toolbox/store/StoreKeys.kt
@@ -36,6 +36,8 @@ internal const val TLS_CA_PATH = "tlsCAPath"
 
 internal const val TLS_ALTERNATE_HOSTNAME = "tlsAlternateHostname"
 
+internal const val TLS_CERT_REFRESH_COMMAND = "tlsCertRefreshCommand"
+
 internal const val DISABLE_AUTOSTART = "disableAutostart"
 
 internal const val ENABLE_SSH_WILDCARD_CONFIG = "enableSshWildcardConfig"
diff --git a/src/main/kotlin/com/coder/toolbox/util/CoderProtocolHandler.kt b/src/main/kotlin/com/coder/toolbox/util/CoderProtocolHandler.kt
index 8e4dfbb3..113ab9f9 100644
--- a/src/main/kotlin/com/coder/toolbox/util/CoderProtocolHandler.kt
+++ b/src/main/kotlin/com/coder/toolbox/util/CoderProtocolHandler.kt
@@ -70,7 +70,7 @@ open class CoderProtocolHandler(
 
         context.logger.info("Handling $uri...")
         val deploymentURL = resolveDeploymentUrl(params) ?: return
-        val token = if (!context.settingsStore.requireTokenAuth) null else resolveToken(params) ?: return
+        val token = if (!context.settingsStore.requiresTokenAuth) null else resolveToken(params) ?: return
         val workspaceName = resolveWorkspaceName(params) ?: return
 
         suspend fun onConnect(
diff --git a/src/main/kotlin/com/coder/toolbox/util/TLS.kt b/src/main/kotlin/com/coder/toolbox/util/TLS.kt
index 97a5df96..101370d2 100644
--- a/src/main/kotlin/com/coder/toolbox/util/TLS.kt
+++ b/src/main/kotlin/com/coder/toolbox/util/TLS.kt
@@ -280,3 +280,77 @@ class MergedSystemTrustManger(private val otherTrustManager: X509TrustManager) :
     override fun getAcceptedIssuers(): Array<X509Certificate> =
         otherTrustManager.acceptedIssuers + systemTrustManager.acceptedIssuers
 }
+
+class ReloadableX509TrustManager(
+    private val caPath: String?,
+) : X509TrustManager {
+    @Volatile
+    private var delegate: X509TrustManager = loadTrustManager()
+
+    private fun loadTrustManager(): X509TrustManager {
+        val trustManagers = coderTrustManagers(caPath)
+        return trustManagers.first { it is X509TrustManager } as X509TrustManager
+    }
+
+    fun reload() {
+        delegate = loadTrustManager()
+    }
+
+    override fun checkClientTrusted(chain: Array<out X509Certificate>?, authType: String?) {
+        delegate.checkClientTrusted(chain, authType)
+    }
+
+    override fun checkServerTrusted(chain: Array<out X509Certificate>?, authType: String?) {
+        delegate.checkServerTrusted(chain, authType)
+    }
+
+    override fun getAcceptedIssuers(): Array<X509Certificate> {
+        return delegate.acceptedIssuers
+    }
+}
+
+class ReloadableSSLSocketFactory(
+    private val settings: ReadOnlyTLSSettings,
+) : SSLSocketFactory() {
+    @Volatile
+    private var delegate: SSLSocketFactory = loadSocketFactory()
+
+    private fun loadSocketFactory(): SSLSocketFactory {
+        return coderSocketFactory(settings)
+    }
+
+    fun reload() {
+        delegate = loadSocketFactory()
+    }
+
+    override fun getDefaultCipherSuites(): Array<String> = delegate.defaultCipherSuites
+
+    override fun getSupportedCipherSuites(): Array<String> = delegate.supportedCipherSuites
+
+    override fun createSocket(): Socket = delegate.createSocket()
+
+    override fun createSocket(s: Socket?, host: String?, port: Int, autoClose: Boolean): Socket =
+        delegate.createSocket(s, host, port, autoClose)
+
+    override fun createSocket(host: String?, port: Int): Socket = delegate.createSocket(host, port)
+
+    override fun createSocket(host: String?, port: Int, localHost: InetAddress?, localPort: Int): Socket =
+        delegate.createSocket(host, port, localHost, localPort)
+
+    override fun createSocket(host: InetAddress?, port: Int): Socket = delegate.createSocket(host, port)
+
+    override fun createSocket(address: InetAddress?, port: Int, localAddress: InetAddress?, localPort: Int): Socket =
+        delegate.createSocket(address, port, localAddress, localPort)
+}
+
+class ReloadableTlsContext(
+    settings: ReadOnlyTLSSettings
+) {
+    val sslSocketFactory = ReloadableSSLSocketFactory(settings)
+    val trustManager = ReloadableX509TrustManager(settings.caPath)
+
+    fun reload() {
+        sslSocketFactory.reload()
+        trustManager.reload()
+    }
+}
diff --git a/src/main/kotlin/com/coder/toolbox/views/ConnectStep.kt b/src/main/kotlin/com/coder/toolbox/views/ConnectStep.kt
index b6d0bbba..247d2c42 100644
--- a/src/main/kotlin/com/coder/toolbox/views/ConnectStep.kt
+++ b/src/main/kotlin/com/coder/toolbox/views/ConnectStep.kt
@@ -49,7 +49,7 @@ class ConnectStep(
             context.i18n.pnotr("")
         }
 
-        if (context.settingsStore.requireTokenAuth && CoderCliSetupContext.isNotReadyForAuth()) {
+        if (context.settingsStore.requiresTokenAuth && CoderCliSetupContext.isNotReadyForAuth()) {
             errorField.textState.update {
                 context.i18n.pnotr("URL and token were not properly configured. Please go back and provide a proper URL and token!")
             }
@@ -70,7 +70,7 @@ class ConnectStep(
             return
         }
 
-        if (context.settingsStore.requireTokenAuth && !CoderCliSetupContext.hasToken()) {
+        if (context.settingsStore.requiresTokenAuth && !CoderCliSetupContext.hasToken()) {
             errorField.textState.update { context.i18n.ptrl("Token is required") }
             return
         }
@@ -84,7 +84,7 @@ class ConnectStep(
                 val client = CoderRestClient(
                     context,
                     url,
-                    if (context.settingsStore.requireTokenAuth) CoderCliSetupContext.token else null,
+                    if (context.settingsStore.requiresTokenAuth) CoderCliSetupContext.token else null,
                     PluginManager.pluginInfo.version,
                 )
                 // allows interleaving with the back/cancel action
@@ -98,7 +98,7 @@ class ConnectStep(
                     statusField.textState.update { (context.i18n.pnotr(progress)) }
                 }
                 // We only need to log in if we are using token-based auth.
-                if (context.settingsStore.requireTokenAuth) {
+                if (context.settingsStore.requiresTokenAuth) {
                     logAndReportProgress("Configuring Coder CLI...")
                     // allows interleaving with the back/cancel action
                     yield()
@@ -144,7 +144,7 @@ class ConnectStep(
                 CoderCliSetupWizardState.goToFirstStep()
             }
         } else {
-            if (context.settingsStore.requireTokenAuth) {
+            if (context.settingsStore.requiresTokenAuth) {
                 CoderCliSetupWizardState.goToPreviousStep()
             } else {
                 CoderCliSetupWizardState.goToFirstStep()
diff --git a/src/main/kotlin/com/coder/toolbox/views/DeploymentUrlStep.kt b/src/main/kotlin/com/coder/toolbox/views/DeploymentUrlStep.kt
index 27e53f97..b4a60668 100644
--- a/src/main/kotlin/com/coder/toolbox/views/DeploymentUrlStep.kt
+++ b/src/main/kotlin/com/coder/toolbox/views/DeploymentUrlStep.kt
@@ -86,7 +86,7 @@ class DeploymentUrlStep(
             errorReporter.report("URL is invalid", e)
             return false
         }
-        if (context.settingsStore.requireTokenAuth) {
+        if (context.settingsStore.requiresTokenAuth) {
             CoderCliSetupWizardState.goToNextStep()
         } else {
             CoderCliSetupWizardState.goToLastStep()
diff --git a/src/test/kotlin/com/coder/toolbox/settings/CoderSettingsTest.kt b/src/test/kotlin/com/coder/toolbox/settings/CoderSettingsTest.kt
index 50334876..9d38c4fe 100644
--- a/src/test/kotlin/com/coder/toolbox/settings/CoderSettingsTest.kt
+++ b/src/test/kotlin/com/coder/toolbox/settings/CoderSettingsTest.kt
@@ -261,19 +261,19 @@ internal class CoderSettingsTest {
     @Test
     fun testRequireTokenAuth() {
         var settings = CoderSettingsStore(pluginTestSettingsStore(), Environment(), logger)
-        assertEquals(true, settings.readOnly().requireTokenAuth)
+        assertEquals(true, settings.readOnly().requiresTokenAuth)
 
         settings = CoderSettingsStore(pluginTestSettingsStore(TLS_CERT_PATH to "cert path"), Environment(), logger)
-        assertEquals(true, settings.readOnly().requireTokenAuth)
+        assertEquals(true, settings.readOnly().requiresTokenAuth)
 
         settings = CoderSettingsStore(pluginTestSettingsStore(TLS_KEY_PATH to "key path"), Environment(), logger)
-        assertEquals(true, settings.readOnly().requireTokenAuth)
+        assertEquals(true, settings.readOnly().requiresTokenAuth)
 
         settings = CoderSettingsStore(
             pluginTestSettingsStore(TLS_CERT_PATH to "cert path", TLS_KEY_PATH to "key path"),
             Environment(), logger
         )
-        assertEquals(false, settings.readOnly().requireTokenAuth)
+        assertEquals(false, settings.readOnly().requiresTokenAuth)
     }
 
     @Test