diff --git a/src/main/kotlin/com/coder/gateway/CoderGatewayConnectionProvider.kt b/src/main/kotlin/com/coder/gateway/CoderGatewayConnectionProvider.kt
index 07b7b961..cd625208 100644
--- a/src/main/kotlin/com/coder/gateway/CoderGatewayConnectionProvider.kt
+++ b/src/main/kotlin/com/coder/gateway/CoderGatewayConnectionProvider.kt
@@ -2,19 +2,29 @@
 
 package com.coder.gateway
 
+import com.coder.gateway.sdk.humanizeDuration
+import com.coder.gateway.sdk.isCancellation
+import com.coder.gateway.sdk.isWorkerTimeout
+import com.coder.gateway.sdk.suspendingRetryWithExponentialBackOff
 import com.coder.gateway.services.CoderRecentWorkspaceConnectionsService
+import com.intellij.openapi.application.ApplicationManager
 import com.intellij.openapi.components.service
 import com.intellij.openapi.diagnostic.Logger
 import com.intellij.openapi.rd.util.launchUnderBackgroundProgress
+import com.intellij.openapi.ui.Messages
 import com.jetbrains.gateway.api.ConnectionRequestor
 import com.jetbrains.gateway.api.GatewayConnectionHandle
 import com.jetbrains.gateway.api.GatewayConnectionProvider
 import com.jetbrains.gateway.api.GatewayUI
 import com.jetbrains.gateway.ssh.SshDeployFlowUtil
 import com.jetbrains.gateway.ssh.SshMultistagePanelContext
+import com.jetbrains.gateway.ssh.deploy.DeployException
 import com.jetbrains.rd.util.lifetime.LifetimeDefinition
 import kotlinx.coroutines.launch
+import net.schmizz.sshj.common.SSHException
+import net.schmizz.sshj.connection.ConnectionException
 import java.time.Duration
+import java.util.concurrent.TimeoutException
 
 class CoderGatewayConnectionProvider : GatewayConnectionProvider {
     private val recentConnectionsService = service<CoderRecentWorkspaceConnectionsService>()
@@ -24,12 +34,53 @@ class CoderGatewayConnectionProvider : GatewayConnectionProvider {
         // TODO: If this fails determine if it is an auth error and if so prompt
         // for a new token, configure the CLI, then try again.
         clientLifetime.launchUnderBackgroundProgress(CoderGatewayBundle.message("gateway.connector.coder.connection.provider.title"), canBeCancelled = true, isIndeterminate = true, project = null) {
-            val context = SshMultistagePanelContext(parameters.toHostDeployInputs())
-            logger.info("Deploying and starting IDE with $context")
-            launch {
-                @Suppress("UnstableApiUsage") SshDeployFlowUtil.fullDeployCycle(
-                    clientLifetime, context, Duration.ofMinutes(10)
+            try {
+                indicator.text = CoderGatewayBundle.message("gateway.connector.coder.connecting")
+                val context = suspendingRetryWithExponentialBackOff(
+                    action = { attempt ->
+                        logger.info("Connecting... (attempt $attempt")
+                        if (attempt > 1) {
+                            // indicator.text is the text above the progress bar.
+                            indicator.text = CoderGatewayBundle.message("gateway.connector.coder.connecting.retry", attempt)
+                        }
+                        SshMultistagePanelContext(parameters.toHostDeployInputs())
+                    },
+                    retryIf = {
+                        it is ConnectionException || it is TimeoutException
+                                || it is SSHException || it is DeployException
+                    },
+                    onException = { attempt, nextMs, e ->
+                        logger.error("Failed to connect (attempt $attempt; will retry in $nextMs ms)")
+                        // indicator.text2 is the text below the progress bar.
+                        indicator.text2 =
+                            if (isWorkerTimeout(e)) "Failed to upload worker binary...it may have timed out"
+                            else e.message ?: CoderGatewayBundle.message("gateway.connector.no-details")
+                    },
+                    onCountdown = { remainingMs ->
+                        indicator.text = CoderGatewayBundle.message("gateway.connector.coder.connecting.failed.retry", humanizeDuration(remainingMs))
+                    },
                 )
+                launch {
+                    logger.info("Deploying and starting IDE with $context")
+                    // At this point JetBrains takes over with their own UI.
+                    @Suppress("UnstableApiUsage") SshDeployFlowUtil.fullDeployCycle(
+                        clientLifetime, context, Duration.ofMinutes(10)
+                    )
+                }
+            } catch (e: Exception) {
+                if (isCancellation(e)) {
+                    logger.info("Connection canceled due to ${e.javaClass}")
+                } else {
+                    logger.info("Failed to connect (will not retry)", e)
+                    // The dialog will close once we return so write the error
+                    // out into a new dialog.
+                    ApplicationManager.getApplication().invokeAndWait {
+                        Messages.showMessageDialog(
+                            e.message ?: CoderGatewayBundle.message("gateway.connector.no-details"),
+                            CoderGatewayBundle.message("gateway.connector.coder.connection.failed"),
+                            Messages.getErrorIcon())
+                    }
+                }
             }
         }
 
diff --git a/src/main/kotlin/com/coder/gateway/sdk/Retry.kt b/src/main/kotlin/com/coder/gateway/sdk/Retry.kt
index 23e6e650..51d4c04c 100644
--- a/src/main/kotlin/com/coder/gateway/sdk/Retry.kt
+++ b/src/main/kotlin/com/coder/gateway/sdk/Retry.kt
@@ -1,23 +1,50 @@
 package com.coder.gateway.sdk
 
+import com.intellij.openapi.progress.ProcessCanceledException
+import com.intellij.ssh.SshException
+import com.jetbrains.gateway.ssh.deploy.DeployException
 import kotlinx.coroutines.delay
-import kotlinx.datetime.Clock
 import java.util.Random
 import java.util.concurrent.TimeUnit
-import kotlin.concurrent.timer
-import kotlin.math.max
+import kotlin.coroutines.cancellation.CancellationException
 import kotlin.math.min
 
+fun unwrap(ex: Exception): Throwable {
+    var cause = ex.cause
+    while(cause?.cause != null) {
+        cause = cause.cause
+    }
+    return cause ?: ex
+}
+
 /**
- * Similar to Intellij's except it gives you the next delay, does not do its own
- * logging, updates periodically (for counting down), and runs forever.
+ * Similar to Intellij's except it adds two new arguments: onCountdown (for
+ * displaying the time until the next try) and retryIf (to limit which
+ * exceptions can be retried).
+ *
+ * Exceptions that cannot be retried will be thrown.
+ *
+ * onException and onCountdown will be called immediately on retryable failures.
+ * onCountdown will also be called every second until the next try with the time
+ * left until that next try (the last interval might be less than one second if
+ * the total delay is not divisible by one second).
+ *
+ * Some other differences:
+ * - onException gives you the time until the next try (intended to be logged
+ *   with the error).
+ * - Infinite tries.
+ * - SshException is unwrapped.
+ *
+ * It is otherwise identical.
  */
 suspend fun <T> suspendingRetryWithExponentialBackOff(
     initialDelayMs: Long = TimeUnit.SECONDS.toMillis(5),
     backOffLimitMs: Long = TimeUnit.MINUTES.toMillis(3),
     backOffFactor: Int = 2,
     backOffJitter: Double = 0.1,
-    update: (attempt: Int, remainingMs: Long, e: Exception) -> Unit,
+    retryIf: (e: Throwable) -> Boolean,
+    onException: (attempt: Int, nextMs: Long, e: Throwable) -> Unit,
+    onCountdown: (remaining: Long) -> Unit,
     action: suspend (attempt: Int) -> T
 ): T {
     val random = Random()
@@ -26,21 +53,53 @@ suspend fun <T> suspendingRetryWithExponentialBackOff(
       try {
           return action(attempt)
       }
-      catch (e: Exception) {
-          val end = Clock.System.now().toEpochMilliseconds() + delayMs
-          val timer = timer(period = TimeUnit.SECONDS.toMillis(1)) {
-              val now = Clock.System.now().toEpochMilliseconds()
-              val next = max(end - now, 0)
-              if (next > 0) {
-                  update(attempt, next, e)
-              } else {
-                  this.cancel()
-              }
+      catch (originalEx: Exception) {
+          // SshException can happen due to anything from a timeout to being
+          // canceled so unwrap to find out.
+          val unwrappedEx = if (originalEx is SshException) unwrap(originalEx) else originalEx
+          if (!retryIf(unwrappedEx)) {
+              throw unwrappedEx
+          }
+          onException(attempt, delayMs, unwrappedEx)
+          var remainingMs = delayMs
+          while (remainingMs > 0) {
+              onCountdown(remainingMs)
+              val next = min(remainingMs, TimeUnit.SECONDS.toMillis(1))
+              remainingMs -= next
+              delay(next)
           }
-          delay(delayMs)
-          timer.cancel()
           delayMs = min(delayMs * backOffFactor, backOffLimitMs) + (random.nextGaussian() * delayMs * backOffJitter).toLong()
       }
     }
     error("Should never be reached")
 }
+
+/**
+ * Convert a millisecond duration into a human-readable string.
+ *
+ * < 1 second: "now"
+ * 1 second: "in one second"
+ * > 1 second: "in <duration> seconds"
+ */
+fun humanizeDuration(durationMs: Long): String {
+    val seconds = TimeUnit.MILLISECONDS.toSeconds(durationMs)
+    return if (seconds < 1) "now" else "in $seconds second${if (seconds > 1) "s" else ""}"
+}
+
+/**
+ * When the worker upload times out Gateway just says it failed. Even the root
+ * cause (IllegalStateException) is useless.  The error also includes a very
+ * long useless tmp path.  Return true if the error looks like this timeout.
+ */
+fun isWorkerTimeout(e: Throwable): Boolean {
+    return e is DeployException && e.message.contains("Worker binary deploy failed")
+}
+
+/**
+ * Return true if the exception is some kind of cancellation.
+ */
+fun isCancellation(e: Throwable): Boolean {
+    return e is InterruptedException
+            || e is CancellationException
+            || e is ProcessCanceledException
+}
diff --git a/src/main/kotlin/com/coder/gateway/views/steps/CoderLocateRemoteProjectStepView.kt b/src/main/kotlin/com/coder/gateway/views/steps/CoderLocateRemoteProjectStepView.kt
index 3154bbd4..3b209edd 100644
--- a/src/main/kotlin/com/coder/gateway/views/steps/CoderLocateRemoteProjectStepView.kt
+++ b/src/main/kotlin/com/coder/gateway/views/steps/CoderLocateRemoteProjectStepView.kt
@@ -8,6 +8,9 @@ import com.coder.gateway.sdk.Arch
 import com.coder.gateway.sdk.CoderCLIManager
 import com.coder.gateway.sdk.CoderRestClientService
 import com.coder.gateway.sdk.OS
+import com.coder.gateway.sdk.humanizeDuration
+import com.coder.gateway.sdk.isCancellation
+import com.coder.gateway.sdk.isWorkerTimeout
 import com.coder.gateway.sdk.suspendingRetryWithExponentialBackOff
 import com.coder.gateway.sdk.toURL
 import com.coder.gateway.sdk.withPath
@@ -68,7 +71,6 @@ import net.schmizz.sshj.connection.ConnectionException
 import java.awt.Component
 import java.awt.FlowLayout
 import java.util.Locale
-import java.util.concurrent.TimeUnit
 import java.util.concurrent.TimeoutException
 import javax.swing.ComboBoxModel
 import javax.swing.DefaultComboBoxModel
@@ -79,7 +81,6 @@ import javax.swing.JPanel
 import javax.swing.ListCellRenderer
 import javax.swing.SwingConstants
 import javax.swing.event.DocumentEvent
-import kotlin.coroutines.cancellation.CancellationException
 
 class CoderLocateRemoteProjectStepView(private val setNextButtonEnabled: (Boolean) -> Unit) : CoderWorkspacesWizardStep, Disposable {
     private val cs = CoroutineScope(Dispatchers.Main)
@@ -162,6 +163,7 @@ class CoderLocateRemoteProjectStepView(private val setNextButtonEnabled: (Boolea
         // Clear contents from the last attempt if any.
         cbIDEComment.foreground = UIUtil.getContextHelpForeground()
         cbIDEComment.text = CoderGatewayBundle.message("gateway.connector.view.coder.remoteproject.ide.none.comment")
+        cbIDE.renderer = IDECellRenderer(CoderGatewayBundle.message("gateway.connector.view.coder.retrieve-ides"))
         ideComboBoxModel.removeAllElements()
         setNextButtonEnabled(false)
 
@@ -178,54 +180,47 @@ class CoderLocateRemoteProjectStepView(private val setNextButtonEnabled: (Boolea
         terminalLink.url = coderClient.coderURL.withPath("/@${coderClient.me.username}/${selectedWorkspace.name}/terminal").toString()
 
         ideResolvingJob = cs.launch {
-            val ides = suspendingRetryWithExponentialBackOff(
-                action={ attempt ->
-                    // Reset text in the select dropdown.
-                    withContext(Dispatchers.Main) {
-                        cbIDE.renderer = IDECellRenderer(
-                            if (attempt > 1) CoderGatewayBundle.message("gateway.connector.view.coder.remoteproject.retry.text", attempt)
-                            else CoderGatewayBundle.message("gateway.connector.view.coder.remoteproject.loading.text"))
-                    }
-                    try {
+            try {
+                val ides = suspendingRetryWithExponentialBackOff(
+                    action = { attempt ->
+                        logger.info("Retrieving IDEs...(attempt $attempt)")
+                        if (attempt > 1) {
+                            cbIDE.renderer = IDECellRenderer(CoderGatewayBundle.message("gateway.connector.view.coder.retrieve.ides.retry", attempt))
+                        }
                         val executor = createRemoteExecutor(CoderCLIManager.getHostName(deploymentURL, selectedWorkspace))
                         if (ComponentValidator.getInstance(tfProject).isEmpty) {
                             installRemotePathValidator(executor)
                         }
                         retrieveIDEs(executor, selectedWorkspace)
-                    } catch (e: Exception) {
-                        when(e) {
-                            is InterruptedException -> Unit
-                            is CancellationException -> Unit
-                            // Throw to retry these.  The main one is
-                            // DeployException which fires when dd times out.
-                            is ConnectionException,  is TimeoutException,
-                            is SSHException, is DeployException -> throw e
-                            else -> {
-                                withContext(Dispatchers.Main) {
-                                    logger.error("Failed to retrieve IDEs (attempt $attempt)", e)
-                                    cbIDEComment.foreground = UIUtil.getErrorForeground()
-                                    cbIDEComment.text = e.message ?: "The error did not provide any further details"
-                                    cbIDE.renderer = IDECellRenderer(CoderGatewayBundle.message("gateway.connector.view.coder.remoteproject.error.text"), UIUtil.getBalloonErrorIcon())
-                                }
-                            }
-                        }
-                        null
-                    }
-                },
-                update = { attempt, retryMs, e ->
-                    logger.error("Failed to retrieve IDEs (attempt $attempt; will retry in $retryMs ms)", e)
-                    cbIDEComment.foreground = UIUtil.getErrorForeground()
-                    cbIDEComment.text = e.message ?: "The error did not provide any further details"
-                    val delayS = TimeUnit.MILLISECONDS.toSeconds(retryMs)
-                    val delay = if (delayS < 1) "now" else "in $delayS second${if (delayS > 1) "s" else ""}"
-                    cbIDE.renderer = IDECellRenderer(CoderGatewayBundle.message("gateway.connector.view.coder.remoteproject.retry-error.text", delay))
-                },
-            )
-            if (ides != null) {
+                    },
+                    retryIf = {
+                        it is ConnectionException || it is TimeoutException
+                                || it is SSHException || it is DeployException
+                    },
+                    onException = { attempt, nextMs, e ->
+                        logger.error("Failed to retrieve IDEs (attempt $attempt; will retry in $nextMs ms)")
+                        cbIDEComment.foreground = UIUtil.getErrorForeground()
+                        cbIDEComment.text =
+                            if (isWorkerTimeout(e)) "Failed to upload worker binary...it may have timed out.  Check the command log for more details."
+                            else e.message ?: CoderGatewayBundle.message("gateway.connector.no-details")
+                    },
+                    onCountdown = { remainingMs ->
+                        cbIDE.renderer = IDECellRenderer(CoderGatewayBundle.message("gateway.connector.view.coder.retrieve-ides.failed.retry", humanizeDuration(remainingMs)))
+                    },
+                )
                 withContext(Dispatchers.Main) {
                     ideComboBoxModel.addAll(ides)
                     cbIDE.selectedIndex = 0
                 }
+            } catch (e: Exception) {
+                if (isCancellation(e)) {
+                    logger.info("Connection canceled due to ${e.javaClass}")
+                } else {
+                    logger.error("Failed to retrieve IDEs (will not retry)", e)
+                    cbIDEComment.foreground = UIUtil.getErrorForeground()
+                    cbIDEComment.text = e.message ?: CoderGatewayBundle.message("gateway.connector.no-details")
+                    cbIDE.renderer = IDECellRenderer(CoderGatewayBundle.message("gateway.connector.view.coder.retrieve-ides.failed"), UIUtil.getBalloonErrorIcon())
+                }
             }
         }
     }
diff --git a/src/main/resources/messages/CoderGatewayBundle.properties b/src/main/resources/messages/CoderGatewayBundle.properties
index d8295e5c..c5e7e8b0 100644
--- a/src/main/resources/messages/CoderGatewayBundle.properties
+++ b/src/main/resources/messages/CoderGatewayBundle.properties
@@ -28,10 +28,10 @@ gateway.connector.view.workspaces.token.comment=The last used token is shown abo
 gateway.connector.view.workspaces.token.rejected=This token was rejected.
 gateway.connector.view.workspaces.token.injected=This token was pulled from your CLI config.
 gateway.connector.view.workspaces.token.none=No existing token found.
-gateway.connector.view.coder.remoteproject.loading.text=Retrieving products...
-gateway.connector.view.coder.remoteproject.retry.text=Retrieving products (attempt {0})...
-gateway.connector.view.coder.remoteproject.error.text=Failed to retrieve IDEs
-gateway.connector.view.coder.remoteproject.retry-error.text=Failed to retrieve IDEs...retrying {0}
+gateway.connector.view.coder.retrieve-ides=Retrieving IDEs...
+gateway.connector.view.coder.retrieve.ides.retry=Retrieving IDEs (attempt {0})...
+gateway.connector.view.coder.retrieve-ides.failed=Failed to retrieve IDEs
+gateway.connector.view.coder.retrieve-ides.failed.retry=Failed to retrieve IDEs...retrying {0}
 gateway.connector.view.coder.remoteproject.next.text=Start IDE and connect
 gateway.connector.view.coder.remoteproject.choose.text=Choose IDE and project for workspace {0}
 gateway.connector.view.coder.remoteproject.ide.download.comment=This IDE will be downloaded from jetbrains.com and installed to the default path on the remote host.
@@ -42,6 +42,10 @@ gateway.connector.recentconnections.new.wizard.button.tooltip=Open a new Coder W
 gateway.connector.recentconnections.remove.button.tooltip=Remove from Recent Connections
 gateway.connector.recentconnections.terminal.button.tooltip=Open SSH Web Terminal
 gateway.connector.coder.connection.provider.title=Connecting to Coder workspace...
+gateway.connector.coder.connecting=Connecting...
+gateway.connector.coder.connecting.retry=Connecting (attempt {0})...
+gateway.connector.coder.connection.failed=Failed to connect
+gateway.connector.coder.connecting.failed.retry=Failed to connect...retrying {0}
 gateway.connector.settings.binary-source.title=CLI source:
 gateway.connector.settings.binary-source.comment=Used to download the Coder \
   CLI which is necessary to make SSH connections. The If-None-Matched header \
@@ -54,3 +58,4 @@ gateway.connector.settings.binary-destination.comment=Directories are created \
   here that store the CLI and credentials for each domain to which the plugin \
   connects. \
   Defaults to {0}.
+gateway.connector.no-details="The error did not provide any further details"