diff --git a/CHANGELOG.md b/CHANGELOG.md
index d161afe..3b6e569 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,10 @@
 
 ## Unreleased
 
+### Changed
+
+- improved workflow when network connection is flaky
+
 ## 0.5.2 - 2025-07-22
 
 ### Fixed
diff --git a/gradle.properties b/gradle.properties
index e6dc4d8..0becc24 100644
--- a/gradle.properties
+++ b/gradle.properties
@@ -1,3 +1,3 @@
-version=0.5.2
+version=0.6.0
 group=com.coder.toolbox
-name=coder-toolbox
+name=coder-toolbox
\ No newline at end of file
diff --git a/src/main/kotlin/com/coder/toolbox/CoderRemoteEnvironment.kt b/src/main/kotlin/com/coder/toolbox/CoderRemoteEnvironment.kt
index 08f5a07..f8b3a17 100644
--- a/src/main/kotlin/com/coder/toolbox/CoderRemoteEnvironment.kt
+++ b/src/main/kotlin/com/coder/toolbox/CoderRemoteEnvironment.kt
@@ -68,6 +68,13 @@ class CoderRemoteEnvironment(
     private val proxyCommandHandle = SshCommandProcessHandle(context)
     private var pollJob: Job? = null
 
+    init {
+        if (context.settingsStore.shouldAutoConnect(id)) {
+            context.logger.info("resuming SSH connection to $id — last session was still active.")
+            startSshConnection()
+        }
+    }
+
     fun asPairOfWorkspaceAndAgent(): Pair<Workspace, WorkspaceAgent> = Pair(workspace, agent)
 
     private fun getAvailableActions(): List<ActionDescription> {
@@ -158,6 +165,7 @@ class CoderRemoteEnvironment(
     override fun beforeConnection() {
         context.logger.info("Connecting to $id...")
         isConnected.update { true }
+        context.settingsStore.updateAutoConnect(this.id, true)
         pollJob = pollNetworkMetrics()
     }
 
@@ -180,12 +188,9 @@ class CoderRemoteEnvironment(
             }
             context.logger.debug("Loading metrics from ${metricsFile.absolutePath} for $id")
             try {
-                val metrics = networkMetricsMarshaller.fromJson(metricsFile.readText())
-                if (metrics == null) {
-                    return@launch
-                }
+                val metrics = networkMetricsMarshaller.fromJson(metricsFile.readText()) ?: return@launch
                 context.logger.debug("$id metrics: $metrics")
-                additionalEnvironmentInformation.put(context.i18n.ptrl("Network Status"), metrics.toPretty())
+                additionalEnvironmentInformation[context.i18n.ptrl("Network Status")] = metrics.toPretty()
             } catch (e: Exception) {
                 context.logger.error(
                     e,
@@ -203,6 +208,10 @@ class CoderRemoteEnvironment(
         pollJob?.cancel()
         this.connectionRequest.update { false }
         isConnected.update { false }
+        if (isManual) {
+            // if the user manually disconnects the ssh connection we should not connect automatically
+            context.settingsStore.updateAutoConnect(this.id, false)
+        }
         context.logger.info("Disconnected from $id")
     }
 
diff --git a/src/main/kotlin/com/coder/toolbox/CoderRemoteProvider.kt b/src/main/kotlin/com/coder/toolbox/CoderRemoteProvider.kt
index d68b077..2e5d557 100644
--- a/src/main/kotlin/com/coder/toolbox/CoderRemoteProvider.kt
+++ b/src/main/kotlin/com/coder/toolbox/CoderRemoteProvider.kt
@@ -80,6 +80,8 @@ class CoderRemoteProvider(
         )
     )
 
+    private val errorBuffer = mutableListOf<Throwable>()
+
     /**
      * With the provided client, start polling for workspaces.  Every time a new
      * workspace is added, reconfigure SSH using the provided cli (including the
@@ -160,23 +162,20 @@ class CoderRemoteProvider(
             } catch (ex: Exception) {
                 val elapsed = lastPollTime.elapsedNow()
                 if (elapsed > POLL_INTERVAL * 2) {
-                    context.logger.info("wake-up from an OS sleep was detected, going to re-initialize the http client...")
-                    client.setupSession()
+                    context.logger.info("wake-up from an OS sleep was detected")
                 } else {
-                    context.logger.error(ex, "workspace polling error encountered, trying to auto-login")
+                    context.logger.error(ex, "workspace polling error encountered")
                     if (ex is APIResponseException && ex.isTokenExpired) {
                         WorkspaceConnectionManager.shouldEstablishWorkspaceConnections = true
+                        close()
+                        context.envPageManager.showPluginEnvironmentsPage()
+                        errorBuffer.add(ex)
+                        break
                     }
-                    close()
-                    // force auto-login
-                    firstRun = true
-                    context.envPageManager.showPluginEnvironmentsPage()
-                    break
                 }
             }
 
-            // TODO: Listening on a web socket might be better?
-            select<Unit> {
+            select {
                 onTimeout(POLL_INTERVAL) {
                     context.logger.trace("workspace poller waked up by the $POLL_INTERVAL timeout")
                 }
@@ -196,9 +195,6 @@ class CoderRemoteProvider(
      * first page.
      */
     private fun logout() {
-        // Keep the URL and token to make it easy to log back in, but set
-        // rememberMe to false so we do not try to automatically log in.
-        context.secrets.rememberMe = false
         WorkspaceConnectionManager.reset()
         close()
     }
@@ -360,22 +356,17 @@ class CoderRemoteProvider(
     override fun getOverrideUiPage(): UiPage? {
         // Show the setup page if we have not configured the client yet.
         if (client == null) {
-            val errorBuffer = mutableListOf<Throwable>()
             // When coming back to the application, initializeSession immediately.
-            val autoSetup = shouldDoAutoSetup()
-            context.secrets.lastToken.let { lastToken ->
-                context.secrets.lastDeploymentURL.let { lastDeploymentURL ->
-                    if (autoSetup && lastDeploymentURL.isNotBlank() && (lastToken.isNotBlank() || !settings.requireTokenAuth)) {
-                        try {
-                            CoderCliSetupWizardState.goToStep(WizardStep.CONNECT)
-                            return CoderCliSetupWizardPage(context, settingsPage, visibilityState, true, ::onConnect)
-                        } catch (ex: Exception) {
-                            errorBuffer.add(ex)
-                        }
-                    }
+            if (shouldDoAutoSetup()) {
+                try {
+                    CoderCliSetupWizardState.goToStep(WizardStep.CONNECT)
+                    return CoderCliSetupWizardPage(context, settingsPage, visibilityState, true, ::onConnect)
+                } catch (ex: Exception) {
+                    errorBuffer.add(ex)
+                } finally {
+                    firstRun = false
                 }
             }
-            firstRun = false
 
             // Login flow.
             val setupWizardPage =
@@ -384,21 +375,24 @@ class CoderRemoteProvider(
             errorBuffer.forEach {
                 setupWizardPage.notify("Error encountered", it)
             }
+            errorBuffer.clear()
             // and now reset the errors, otherwise we show it every time on the screen
             return setupWizardPage
         }
         return null
     }
 
-    private fun shouldDoAutoSetup(): Boolean = firstRun && context.secrets.rememberMe == true
+    /**
+     * 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 && (context.secrets.canAutoLogin || !settings.requireTokenAuth)
 
     private fun onConnect(client: CoderRestClient, cli: CoderCLIManager) {
         // Store the URL and token for use next time.
         context.secrets.lastDeploymentURL = client.url.toString()
         context.secrets.lastToken = client.token ?: ""
         context.secrets.storeTokenFor(client.url, context.secrets.lastToken)
-        // Currently we always remember, but this could be made an option.
-        context.secrets.rememberMe = true
         this.client = client
         pollJob?.cancel()
         environments.showLoadingMessage()
diff --git a/src/main/kotlin/com/coder/toolbox/sdk/CoderRestClient.kt b/src/main/kotlin/com/coder/toolbox/sdk/CoderRestClient.kt
index e3a882f..1a0f18e 100644
--- a/src/main/kotlin/com/coder/toolbox/sdk/CoderRestClient.kt
+++ b/src/main/kotlin/com/coder/toolbox/sdk/CoderRestClient.kt
@@ -60,7 +60,7 @@ open class CoderRestClient(
         setupSession()
     }
 
-    fun setupSession() {
+    private fun setupSession() {
         moshi =
             Moshi.Builder()
                 .add(ArchConverter())
diff --git a/src/main/kotlin/com/coder/toolbox/settings/ReadOnlyCoderSettings.kt b/src/main/kotlin/com/coder/toolbox/settings/ReadOnlyCoderSettings.kt
index a6d6143..693c1fd 100644
--- a/src/main/kotlin/com/coder/toolbox/settings/ReadOnlyCoderSettings.kt
+++ b/src/main/kotlin/com/coder/toolbox/settings/ReadOnlyCoderSettings.kt
@@ -146,6 +146,11 @@ interface ReadOnlyCoderSettings {
      * Return the URL and token from the config, if they exist.
      */
     fun readConfig(dir: Path): Pair<String?, String?>
+
+    /**
+     * Returns whether the SSH connection should be automatically established.
+     */
+    fun shouldAutoConnect(workspaceId: String): Boolean
 }
 
 /**
diff --git a/src/main/kotlin/com/coder/toolbox/store/CoderSecretsStore.kt b/src/main/kotlin/com/coder/toolbox/store/CoderSecretsStore.kt
index 3170a06..a807b69 100644
--- a/src/main/kotlin/com/coder/toolbox/store/CoderSecretsStore.kt
+++ b/src/main/kotlin/com/coder/toolbox/store/CoderSecretsStore.kt
@@ -24,9 +24,8 @@ class CoderSecretsStore(private val store: PluginSecretStore) {
     var lastToken: String
         get() = get("last-token")
         set(value) = set("last-token", value)
-    var rememberMe: Boolean
-        get() = get("remember-me").toBoolean()
-        set(value) = set("remember-me", value.toString())
+    val canAutoLogin: Boolean
+        get() = lastDeploymentURL.isNotBlank() && lastToken.isNotBlank()
 
     fun tokenFor(url: URL): String? = store[url.host]
 
diff --git a/src/main/kotlin/com/coder/toolbox/store/CoderSettingsStore.kt b/src/main/kotlin/com/coder/toolbox/store/CoderSettingsStore.kt
index ff56380..0fa4914 100644
--- a/src/main/kotlin/com/coder/toolbox/store/CoderSettingsStore.kt
+++ b/src/main/kotlin/com/coder/toolbox/store/CoderSettingsStore.kt
@@ -142,6 +142,10 @@ class CoderSettingsStore(
                 }
     }
 
+    override fun shouldAutoConnect(workspaceId: String): Boolean {
+        return store["$SSH_AUTO_CONNECT_PREFIX$workspaceId"]?.toBooleanStrictOrNull() ?: false
+    }
+
     // a readonly cast
     fun readOnly(): ReadOnlyCoderSettings = this
 
@@ -213,6 +217,10 @@ class CoderSettingsStore(
         store[SSH_CONFIG_OPTIONS] = options
     }
 
+    fun updateAutoConnect(workspaceId: String, autoConnect: Boolean) {
+        store["$SSH_AUTO_CONNECT_PREFIX$workspaceId"] = autoConnect.toString()
+    }
+
     private fun getDefaultGlobalDataDir(): Path {
         return when (getOS()) {
             OS.WINDOWS -> Paths.get(env.get("LOCALAPPDATA"), "coder-toolbox")
diff --git a/src/main/kotlin/com/coder/toolbox/store/StoreKeys.kt b/src/main/kotlin/com/coder/toolbox/store/StoreKeys.kt
index 91e3b74..cd1a05d 100644
--- a/src/main/kotlin/com/coder/toolbox/store/StoreKeys.kt
+++ b/src/main/kotlin/com/coder/toolbox/store/StoreKeys.kt
@@ -42,3 +42,5 @@ internal const val SSH_CONFIG_OPTIONS = "sshConfigOptions"
 
 internal const val NETWORK_INFO_DIR = "networkInfoDir"
 
+internal const val SSH_AUTO_CONNECT_PREFIX = "ssh_auto_connect_"
+
diff --git a/src/main/kotlin/com/coder/toolbox/views/ConnectStep.kt b/src/main/kotlin/com/coder/toolbox/views/ConnectStep.kt
index e01971c..7ea93e4 100644
--- a/src/main/kotlin/com/coder/toolbox/views/ConnectStep.kt
+++ b/src/main/kotlin/com/coder/toolbox/views/ConnectStep.kt
@@ -128,7 +128,6 @@ class ConnectStep(
             if (shouldAutoLogin.value) {
                 CoderCliSetupContext.reset()
                 CoderCliSetupWizardState.goToFirstStep()
-                context.secrets.rememberMe = false
             } else {
                 if (context.settingsStore.requireTokenAuth) {
                     CoderCliSetupWizardState.goToPreviousStep()

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