diff --git a/engine/launcher/src/main/scala/org/enso/launcher/InfoLogger.scala b/engine/launcher/src/main/scala/org/enso/launcher/InfoLogger.scala
index 60fd96d696..9819994681 100644
--- a/engine/launcher/src/main/scala/org/enso/launcher/InfoLogger.scala
+++ b/engine/launcher/src/main/scala/org/enso/launcher/InfoLogger.scala
@@ -1,6 +1,5 @@
 package org.enso.launcher
 
-import com.typesafe.scalalogging.Logger
 import org.enso.cli.CLIOutput
 
 /** Handles displaying of user-facing information.
@@ -11,23 +10,12 @@ import org.enso.cli.CLIOutput
   */
 object InfoLogger {
 
-  private val logger = Logger("launcher")
-
   /** Prints an info level message.
     *
-    * If the default logger is set-up to display info-messages, they are send to
-    * the logger, otherwise they are printed to stdout.
-    *
-    * It is important to note that these messages should always be displayed to
-    * the user, so unless run in debug mode, all launcher settings should ensure
-    * that info-level logs are printed to the console output.
+    * Currently, the message is always printed to standard output. But this may be changed by changing this method.
     */
   def info(msg: => String): Unit = {
-    if (logger.underlying.isInfoEnabled) {
-      logger.info(msg)
-    } else {
-      CLIOutput.println(msg)
-    }
+    CLIOutput.println(msg)
   }
 
 }
diff --git a/engine/launcher/src/main/scala/org/enso/launcher/releases/LauncherRepository.scala b/engine/launcher/src/main/scala/org/enso/launcher/releases/LauncherRepository.scala
index 86aa35c385..68cdae632e 100644
--- a/engine/launcher/src/main/scala/org/enso/launcher/releases/LauncherRepository.scala
+++ b/engine/launcher/src/main/scala/org/enso/launcher/releases/LauncherRepository.scala
@@ -33,6 +33,9 @@ object LauncherRepository {
   private val launcherFallbackProviderHostname =
     "launcherfallback.release.enso.org"
 
+  /** URL to the repo that could be displayed to the user. */
+  def websiteUrl: String = "https://github.com/enso-org/enso"
+
   /** Defines a part of the URL scheme of the fallback mechanism - the name of
     * the directory that holds the releases.
     *
diff --git a/engine/launcher/src/main/scala/org/enso/launcher/releases/launcher/LauncherReleaseProvider.scala b/engine/launcher/src/main/scala/org/enso/launcher/releases/launcher/LauncherReleaseProvider.scala
index 2626964c54..f37000069e 100644
--- a/engine/launcher/src/main/scala/org/enso/launcher/releases/launcher/LauncherReleaseProvider.scala
+++ b/engine/launcher/src/main/scala/org/enso/launcher/releases/launcher/LauncherReleaseProvider.scala
@@ -29,8 +29,7 @@ class LauncherReleaseProvider(releaseProvider: SimpleReleaseProvider)
           .find(_.fileName == LauncherManifest.assetName)
           .toRight(
             ReleaseProviderException(
-              s"${LauncherManifest.assetName} file is missing from release " +
-              s"assets."
+              s"${LauncherManifest.assetName} file is missing from $tag release assets."
             )
           )
           .toTry
diff --git a/engine/launcher/src/main/scala/org/enso/launcher/upgrade/LauncherUpgrader.scala b/engine/launcher/src/main/scala/org/enso/launcher/upgrade/LauncherUpgrader.scala
index 24aa97a192..ad37d86fca 100644
--- a/engine/launcher/src/main/scala/org/enso/launcher/upgrade/LauncherUpgrader.scala
+++ b/engine/launcher/src/main/scala/org/enso/launcher/upgrade/LauncherUpgrader.scala
@@ -1,6 +1,6 @@
 package org.enso.launcher.upgrade
 
-import java.nio.file.{Files, Path}
+import java.nio.file.{AccessDeniedException, Files, Path}
 import com.typesafe.scalalogging.Logger
 import org.enso.semver.SemVer
 import org.enso.semver.SemVerOrdering._
@@ -24,7 +24,7 @@ import org.enso.launcher.cli.{
 import org.enso.launcher.releases.launcher.LauncherRelease
 import org.enso.runtimeversionmanager.releases.ReleaseProvider
 import org.enso.launcher.releases.LauncherRepository
-import org.enso.launcher.InfoLogger
+import org.enso.launcher.{Constants, InfoLogger}
 import org.enso.launcher.distribution.DefaultManagers
 import org.enso.runtimeversionmanager.locking.Resources
 import org.slf4j.LoggerFactory
@@ -97,12 +97,45 @@ class LauncherUpgrader(
           }
         }
       }
-      if (release.canPerformUpgradeFromCurrentVersion)
+
+      val canPerformDirectUpgrade: Boolean =
+        if (release.canPerformUpgradeFromCurrentVersion) true
+        else if (CurrentVersion.isDevVersion) {
+          logger.warn(
+            s"Cannot upgrade to version ${release.version} directly, because " +
+            s"it requires at least version " +
+            s"${release.minimumVersionToPerformUpgrade}."
+          )
+          if (globalCLIOptions.autoConfirm) {
+            logger.warn(
+              s"However, the current version (${CurrentVersion.version}) is " +
+              s"a development version, so the minimum version check can be " +
+              s"ignored. Since `auto-confirm` is set, the upgrade will " +
+              s"continue. But please be warned that it may fail due to " +
+              s"incompatibility."
+            )
+            true
+          } else {
+            logger.warn(
+              s"Since the current version (${CurrentVersion.version}) is " +
+              s"a development version, the minimum version check can be " +
+              s"ignored. However, please be warned that the upgrade " +
+              s"may fail due to incompatibility."
+            )
+            CLIOutput.askConfirmation(
+              "Do you want to continue upgrading to this version " +
+              "despite the warning?"
+            )
+          }
+        } else false
+
+      if (canPerformDirectUpgrade)
         performUpgradeTo(release)
       else
         performStepByStepUpgrade(release)
 
       runCleanup()
+      logger.debug("Upgrade completed successfully.")
     }
   }
 
@@ -120,11 +153,13 @@ class LauncherUpgrader(
     val temporaryFiles =
       FileSystem.listDirectory(binRoot).filter(isTemporaryExecutable)
     if (temporaryFiles.nonEmpty && isStartup) {
-      logger.debug("Cleaning temporary files from a previous upgrade.")
+      logger.debug(
+        s"Cleaning ${temporaryFiles.size} temporary files from a previous upgrade."
+      )
     }
     for (file <- temporaryFiles) {
       try {
-        Files.delete(file)
+        tryHardToDelete(file)
         logger.debug(s"Upgrade cleanup: removed `$file`.")
       } catch {
         case NonFatal(e) =>
@@ -133,6 +168,21 @@ class LauncherUpgrader(
     }
   }
 
+  /** On Windows, deleting an executable immediately after it has exited may fail
+    * and the process may need to wait a few millisecond. This method detects
+    * this kind of failure and retries a few times.
+    */
+  private def tryHardToDelete(file: Path, attempts: Int = 30): Unit = {
+    try {
+      Files.delete(file)
+    } catch {
+      case _: AccessDeniedException if attempts > 0 =>
+        logger.trace(s"Failed to delete file `$file`. Retrying.")
+        Thread.sleep(100)
+        tryHardToDelete(file, attempts - 1)
+    }
+  }
+
   /** Continues a multi-step upgrade.
     *
     * Called by [[InternalOpts]] when the upgrade continuation is requested by
@@ -217,28 +267,53 @@ class LauncherUpgrader(
 
   @scala.annotation.tailrec
   private def nextVersionToUpgradeTo(
-    release: LauncherRelease,
+    currentTargetRelease: LauncherRelease,
     availableVersions: Seq[SemVer]
   ): LauncherRelease = {
-    val recentEnoughVersions =
-      availableVersions.filter(
-        _.isGreaterThanOrEqual(release.minimumVersionToPerformUpgrade)
+    assert(
+      currentTargetRelease.minimumVersionToPerformUpgrade.isGreaterThan(
+        CurrentVersion.version
       )
+    )
+
+    // We look at older versions that are satisfying the minimum version
+    // required to upgrade to currentTargetRelease.
+    val recentEnoughVersions =
+      availableVersions.filter { possibleVersion =>
+        val canUpgradeToTarget = possibleVersion.isGreaterThanOrEqual(
+          currentTargetRelease.minimumVersionToPerformUpgrade
+        )
+        val isEarlierThanTarget =
+          possibleVersion.isLessThan(currentTargetRelease.version)
+        canUpgradeToTarget && isEarlierThanTarget
+      }
+
+    // We take the oldest of these, hoping that it will yield the shortest
+    // upgrade path (perhaps it will be possible to upgrade directly from
+    // current version)
     val minimumValidVersion = recentEnoughVersions.sorted.headOption.getOrElse {
       throw UpgradeError(
-        s"Upgrade failed: To continue upgrade, a version at least " +
-        s"${release.minimumVersionToPerformUpgrade} is required, but no " +
-        s"valid version satisfying this requirement could be found."
+        s"Upgrade failed: To continue upgrade, at least version " +
+        s"${currentTargetRelease.minimumVersionToPerformUpgrade} is required, " +
+        s"but no upgrade path has been found from the current version " +
+        s"${CurrentVersion.version}. " +
+        s"Please manually download a newer release from " +
+        s"${LauncherRepository.websiteUrl}"
       )
     }
-    val nextRelease = releaseProvider.fetchRelease(minimumValidVersion).get
+
+    val newTargetRelease = releaseProvider.fetchRelease(minimumValidVersion).get
+    assert(newTargetRelease.version != currentTargetRelease.version)
     logger.debug(
-      s"To upgrade to ${release.version}, " +
-      s"the launcher will have to upgrade to ${nextRelease.version} first."
+      s"To upgrade to ${currentTargetRelease.version}, " +
+      s"the launcher will have to upgrade to ${newTargetRelease.version} first."
     )
-    if (nextRelease.canPerformUpgradeFromCurrentVersion)
-      nextRelease
-    else nextVersionToUpgradeTo(nextRelease, availableVersions)
+
+    // If the current version cannot upgrade directly to the new target version,
+    // we continue the search looking for an even earlier version that we could
+    // upgrade to.
+    if (newTargetRelease.canPerformUpgradeFromCurrentVersion) newTargetRelease
+    else nextVersionToUpgradeTo(newTargetRelease, availableVersions)
   }
 
   /** Extracts just the launcher executable from the archive.
@@ -331,7 +406,7 @@ class LauncherUpgrader(
 
       val temporaryExecutable = temporaryExecutablePath("new")
       FileSystem.copyFile(
-        extractedRoot / "bin" / OS.executableName("enso"),
+        extractedRoot / "bin" / OS.executableName(Constants.name),
         temporaryExecutable
       )
 
diff --git a/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.9999.0-marked-broken/launcher-manifest.yaml b/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.1/launcher-manifest.yaml
similarity index 54%
rename from engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.9999.0-marked-broken/launcher-manifest.yaml
rename to engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.1/launcher-manifest.yaml
index c55d8486cd..d961526d03 100644
--- a/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.9999.0-marked-broken/launcher-manifest.yaml
+++ b/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.1/launcher-manifest.yaml
@@ -1,3 +1,3 @@
-minimum-version-for-upgrade: 0.0.2
+minimum-version-for-upgrade: 1.0.0
 files-to-copy: []
 directories-to-copy: []
diff --git a/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.1/enso-launcher-0.0.1-linux-amd64.tar.gz/enso/README.md b/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.2/enso-launcher-1.0.2-linux-amd64.tar.gz/enso/README.md
similarity index 100%
rename from engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.1/enso-launcher-0.0.1-linux-amd64.tar.gz/enso/README.md
rename to engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.2/enso-launcher-1.0.2-linux-amd64.tar.gz/enso/README.md
diff --git a/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.1/enso-launcher-0.0.1-linux-amd64.tar.gz/enso/THIRD-PARTY/test-license.txt b/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.2/enso-launcher-1.0.2-linux-amd64.tar.gz/enso/THIRD-PARTY/test-license.txt
similarity index 100%
rename from engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.1/enso-launcher-0.0.1-linux-amd64.tar.gz/enso/THIRD-PARTY/test-license.txt
rename to engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.2/enso-launcher-1.0.2-linux-amd64.tar.gz/enso/THIRD-PARTY/test-license.txt
diff --git a/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.1/enso-launcher-0.0.1-macos-amd64.tar.gz/enso/README.md b/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.2/enso-launcher-1.0.2-macos-amd64.tar.gz/enso/README.md
similarity index 100%
rename from engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.1/enso-launcher-0.0.1-macos-amd64.tar.gz/enso/README.md
rename to engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.2/enso-launcher-1.0.2-macos-amd64.tar.gz/enso/README.md
diff --git a/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.1/enso-launcher-0.0.1-macos-amd64.tar.gz/enso/THIRD-PARTY/test-license.txt b/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.2/enso-launcher-1.0.2-macos-amd64.tar.gz/enso/THIRD-PARTY/test-license.txt
similarity index 100%
rename from engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.1/enso-launcher-0.0.1-macos-amd64.tar.gz/enso/THIRD-PARTY/test-license.txt
rename to engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.2/enso-launcher-1.0.2-macos-amd64.tar.gz/enso/THIRD-PARTY/test-license.txt
diff --git a/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.1/enso-launcher-0.0.1-windows-amd64.zip/enso/README.md b/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.2/enso-launcher-1.0.2-windows-amd64.zip/enso/README.md
similarity index 100%
rename from engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.1/enso-launcher-0.0.1-windows-amd64.zip/enso/README.md
rename to engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.2/enso-launcher-1.0.2-windows-amd64.zip/enso/README.md
diff --git a/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.1/enso-launcher-0.0.1-windows-amd64.zip/enso/THIRD-PARTY/test-license.txt b/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.2/enso-launcher-1.0.2-windows-amd64.zip/enso/THIRD-PARTY/test-license.txt
similarity index 100%
rename from engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.1/enso-launcher-0.0.1-windows-amd64.zip/enso/THIRD-PARTY/test-license.txt
rename to engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.2/enso-launcher-1.0.2-windows-amd64.zip/enso/THIRD-PARTY/test-license.txt
diff --git a/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.1/launcher-manifest.yaml b/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.2/launcher-manifest.yaml
similarity index 65%
rename from engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.1/launcher-manifest.yaml
rename to engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.2/launcher-manifest.yaml
index 1e112f5462..1150b6ce4c 100644
--- a/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.1/launcher-manifest.yaml
+++ b/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.2/launcher-manifest.yaml
@@ -1,4 +1,4 @@
-minimum-version-for-upgrade: 0.0.0
+minimum-version-for-upgrade: 1.0.1
 files-to-copy:
   - README.md
 directories-to-copy:
diff --git a/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.2/launcher-manifest.yaml b/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.3/launcher-manifest.yaml
similarity index 54%
rename from engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.2/launcher-manifest.yaml
rename to engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.3/launcher-manifest.yaml
index fecb64ecc0..71cbcb4ade 100644
--- a/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.2/launcher-manifest.yaml
+++ b/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.3/launcher-manifest.yaml
@@ -1,3 +1,3 @@
-minimum-version-for-upgrade: 0.0.1
+minimum-version-for-upgrade: 1.0.2
 files-to-copy: []
 directories-to-copy: []
diff --git a/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.3/launcher-manifest.yaml b/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.4/launcher-manifest.yaml
similarity index 54%
rename from engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.3/launcher-manifest.yaml
rename to engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.4/launcher-manifest.yaml
index c55d8486cd..71cbcb4ade 100644
--- a/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.3/launcher-manifest.yaml
+++ b/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-1.0.4/launcher-manifest.yaml
@@ -1,3 +1,3 @@
-minimum-version-for-upgrade: 0.0.2
+minimum-version-for-upgrade: 1.0.2
 files-to-copy: []
 directories-to-copy: []
diff --git a/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.9999.0-marked-broken/broken b/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-99.9999.0/broken
similarity index 100%
rename from engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.9999.0-marked-broken/broken
rename to engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-99.9999.0/broken
diff --git a/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.4/launcher-manifest.yaml b/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-99.9999.0/launcher-manifest.yaml
similarity index 54%
rename from engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.4/launcher-manifest.yaml
rename to engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-99.9999.0/launcher-manifest.yaml
index c55d8486cd..39a7f1724b 100644
--- a/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-0.0.4/launcher-manifest.yaml
+++ b/engine/launcher/src/test/resources/org/enso/launcher/components/fake-releases/launcher/enso-99.9999.0/launcher-manifest.yaml
@@ -1,3 +1,3 @@
-minimum-version-for-upgrade: 0.0.2
+minimum-version-for-upgrade: 0.0.0
 files-to-copy: []
 directories-to-copy: []
diff --git a/engine/launcher/src/test/scala/org/enso/launcher/NativeTest.scala b/engine/launcher/src/test/scala/org/enso/launcher/NativeTest.scala
index b88faedfc2..517cc57cf9 100644
--- a/engine/launcher/src/test/scala/org/enso/launcher/NativeTest.scala
+++ b/engine/launcher/src/test/scala/org/enso/launcher/NativeTest.scala
@@ -58,7 +58,7 @@ trait NativeTest
     args: Seq[String],
     extraEnv: Map[String, String]      = Map.empty,
     extraJVMProps: Map[String, String] = Map.empty,
-    timeoutSeconds: Long               = 15
+    timeoutSeconds: Long               = defaultTimeoutSeconds
   ): RunResult = {
     if (extraEnv.contains("PATH")) {
       throw new IllegalArgumentException(
@@ -89,7 +89,7 @@ trait NativeTest
     args: Seq[String],
     extraEnv: Map[String, String]      = Map.empty,
     extraJVMProps: Map[String, String] = Map.empty,
-    timeoutSeconds: Long               = 15
+    timeoutSeconds: Long               = defaultTimeoutSeconds
   ): RunResult = {
     if (extraEnv.contains("PATH")) {
       throw new IllegalArgumentException(
@@ -146,7 +146,7 @@ trait NativeTest
     args: Seq[String],
     pathOverride: String,
     extraJVMProps: Map[String, String] = Map.empty,
-    timeoutSeconds: Long               = 15
+    timeoutSeconds: Long               = defaultTimeoutSeconds
   ): RunResult = {
     runCommand(
       Seq(baseLauncherLocation.toAbsolutePath.toString) ++ args,
@@ -155,6 +155,8 @@ trait NativeTest
       timeoutSeconds = timeoutSeconds
     )
   }
+
+  private val defaultTimeoutSeconds: Long = 30
 }
 
 object NativeTest {
diff --git a/engine/launcher/src/test/scala/org/enso/launcher/upgrade/UpgradeSpec.scala b/engine/launcher/src/test/scala/org/enso/launcher/upgrade/UpgradeSpec.scala
index 7e941bcbbc..af9577e396 100644
--- a/engine/launcher/src/test/scala/org/enso/launcher/upgrade/UpgradeSpec.scala
+++ b/engine/launcher/src/test/scala/org/enso/launcher/upgrade/UpgradeSpec.scala
@@ -1,24 +1,23 @@
 package org.enso.launcher.upgrade
 
-import java.nio.file.{Files, Path, StandardCopyOption}
 import io.circe.parser
-import org.enso.semver.SemVer
-import org.enso.distribution.FileSystem
-import org.enso.distribution.locking.{FileLockManager, LockType}
-import FileSystem.PathSyntax
 import org.enso.cli.OS
+import org.enso.distribution.FileSystem
+import org.enso.distribution.FileSystem.PathSyntax
+import org.enso.distribution.locking.{FileLockManager, LockType}
 import org.enso.launcher._
-import org.enso.testkit.{FlakySpec, WithTemporaryDirectory}
 import org.enso.process.{RunResult, WrappedProcess}
-import org.enso.version.BuildVersion
+import org.enso.runtimeversionmanager.releases.testing.FakeAsset
+import org.enso.semver.SemVer
+import org.enso.testkit.{FlakySpec, WithTemporaryDirectory}
 import org.scalatest.exceptions.TestFailedException
-import org.scalatest.{BeforeAndAfterAll, Ignore, OptionValues}
+import org.scalatest.{BeforeAndAfterAll, OptionValues}
 
+import java.nio.file.{Files, Path, StandardCopyOption}
 import scala.concurrent.TimeoutException
 
 // TODO [DB] The suite became quite flaky and frequently fails the
 // Windows CI. Disabled until #3183 is implemented.
-@Ignore
 class UpgradeSpec
     extends NativeTest
     with WithTemporaryDirectory
@@ -32,13 +31,14 @@ class UpgradeSpec
 
   /** Location of built Rust artifacts.
     */
-  private val rustBuildRoot = Path.of("./target/rust/debug/")
+  private val rustBuildRoot =
+    Path.of("../../target/rust/debug/").toAbsolutePath.normalize()
 
   /** Location of the actual launcher executable that is wrapped by the shims.
     */
   private val realLauncherLocation =
     Path
-      .of(".")
+      .of("../../")
       .resolve(OS.executableName(Constants.name))
       .toAbsolutePath
       .normalize
@@ -70,10 +70,13 @@ class UpgradeSpec
   override def beforeAll(): Unit = {
     super.beforeAll()
     prepareLauncherBinary(SemVer.of(0, 0, 0))
-    prepareLauncherBinary(SemVer.of(0, 0, 1))
-    prepareLauncherBinary(SemVer.of(0, 0, 2))
-    prepareLauncherBinary(SemVer.of(0, 0, 3))
-    prepareLauncherBinary(SemVer.of(0, 0, 4))
+    prepareLauncherBinary(SemVer.of(1, 0, 1))
+    prepareLauncherBinary(SemVer.of(1, 0, 2))
+    prepareLauncherBinary(SemVer.of(1, 0, 3))
+    prepareLauncherBinary(SemVer.of(1, 0, 4))
+
+    // The 99.9999.0 version is marked as broken so it should not be considered for upgrades.
+    prepareLauncherBinary(SemVer.of(99, 9999, 0))
   }
 
   /** Prepares a launcher distribution in the temporary test location.
@@ -88,7 +91,7 @@ class UpgradeSpec
     */
   private def prepareDistribution(
     portable: Boolean,
-    launcherVersion: Option[SemVer] = None
+    launcherVersion: Option[SemVer]
   ): Unit = {
     val sourceLauncherLocation =
       launcherVersion.map(builtLauncherBinary).getOrElse(baseLauncherLocation)
@@ -172,41 +175,41 @@ class UpgradeSpec
     "upgrade to latest version (excluding broken)" taggedAs Flaky in {
       prepareDistribution(
         portable        = true,
-        launcherVersion = Some(SemVer.of(0, 0, 2))
+        launcherVersion = Some(SemVer.of(1, 0, 2))
       )
       run(Seq("upgrade")) should returnSuccess
 
-      checkVersion() shouldEqual SemVer.of(0, 0, 4)
+      checkVersion() shouldEqual SemVer.of(1, 0, 4)
     }
 
     "not downgrade without being explicitly asked to do so" taggedAs Flaky in {
-      // precondition for the test to make sense
-      SemVer
-        .parse(BuildVersion.ensoVersion)
-        .get
-        .isGreaterThan(SemVer.of(0, 0, 4)) shouldBe true
-
       prepareDistribution(
-        portable = true
+        portable        = false,
+        launcherVersion = Some(SemVer.of(99, 9999, 0))
       )
-      run(Seq("upgrade")).exitCode shouldEqual 1
+
+      // precondition for the test to make sense
+      checkVersion().isGreaterThan(SemVer.of(1, 0, 4)) shouldBe true
+      val result = run(Seq("upgrade"))
+      withClue(result) {
+        result.exitCode shouldEqual 1
+        result.stdout should include("If you really want to downgrade")
+      }
     }
 
     "upgrade/downgrade to a specific version " +
     "(and update necessary files)" taggedAs Flaky in {
-      // precondition for the test to make sense
-      SemVer
-        .parse(BuildVersion.ensoVersion)
-        .get
-        .isGreaterThan(SemVer.of(0, 0, 4)) shouldBe true
-
       prepareDistribution(
-        portable = true
+        portable        = true,
+        launcherVersion = Some(SemVer.of(99, 9999, 0))
       )
+      // precondition for the test to make sense
+      checkVersion().isGreaterThan(SemVer.of(1, 0, 4)) shouldBe true
+
       val root = launcherPath.getParent.getParent
       FileSystem.writeTextFile(root / "README.md", "Old readme")
-      run(Seq("upgrade", "0.0.1")) should returnSuccess
-      checkVersion() shouldEqual SemVer.of(0, 0, 1)
+      run(Seq("upgrade", "1.0.2")) should returnSuccess
+      checkVersion() shouldEqual SemVer.of(1, 0, 2)
       TestHelpers.readFileContent(root / "README.md").trim shouldEqual "Content"
       TestHelpers
         .readFileContent(root / "THIRD-PARTY" / "test-license.txt")
@@ -216,19 +219,21 @@ class UpgradeSpec
     "upgrade also in installed mode" taggedAs Flaky in {
       prepareDistribution(
         portable        = false,
-        launcherVersion = Some(SemVer.of(0, 0, 0))
+        launcherVersion = Some(SemVer.of(1, 0, 1))
       )
       val dataRoot   = getTestDirectory / "data"
       val configRoot = getTestDirectory / "config"
-      checkVersion() shouldEqual SemVer.of(0, 0, 0)
+      checkVersion() shouldEqual SemVer.of(1, 0, 1)
       val env = Map(
         "ENSO_DATA_DIRECTORY"    -> dataRoot.toString,
         "ENSO_CONFIG_DIRECTORY"  -> configRoot.toString,
         "ENSO_RUNTIME_DIRECTORY" -> (getTestDirectory / "run").toString
       )
 
-      run(Seq("upgrade", "0.0.1"), extraEnv = env) should returnSuccess
-      checkVersion() shouldEqual SemVer.of(0, 0, 1)
+      run(Seq("upgrade", "1.0.2"), extraEnv = env) should returnSuccess
+      checkVersion() shouldEqual SemVer.of(1, 0, 2)
+
+      // Make sure that files were added
       TestHelpers
         .readFileContent(dataRoot / "README.md")
         .trim shouldEqual "Content"
@@ -238,27 +243,25 @@ class UpgradeSpec
     }
 
     "perform a multi-step upgrade if necessary" taggedAs Flaky in {
-      // 0.0.3 can only be upgraded from 0.0.2 which can only be upgraded from
-      // 0.0.1, so the upgrade path should be following:
-      // 0.0.0 -> 0.0.1 -> 0.0.2 -> 0.0.3
+      // 1.0.4 can only be upgraded from 1.0.2 which can only be upgraded from
+      // 1.0.1, so the upgrade path should be following: 1.0.1 -> 1.0.2 -> 1.0.4
       prepareDistribution(
         portable        = true,
-        launcherVersion = Some(SemVer.of(0, 0, 0))
+        launcherVersion = Some(SemVer.of(1, 0, 1))
       )
 
-      checkVersion() shouldEqual SemVer.of(0, 0, 0)
-      val process = startLauncher(Seq("upgrade", "0.0.3"))
+      checkVersion() shouldEqual SemVer.of(1, 0, 1)
+      val process = startLauncher(Seq("upgrade", "1.0.4"))
       try {
-        process.join(timeoutSeconds = 30) should returnSuccess
+        process.join(timeoutSeconds = 60) should returnSuccess
 
-        checkVersion() shouldEqual SemVer.of(0, 0, 3)
+        checkVersion() shouldEqual SemVer.of(1, 0, 4)
 
         val launchedVersions = Seq(
-          "0.0.0",
-          "0.0.0",
-          "0.0.1",
-          "0.0.2",
-          "0.0.3"
+          "1.0.1",
+          "1.0.1",
+          "1.0.2",
+          "1.0.4"
         )
 
         val reportedLaunchLog = TestHelpers
@@ -294,7 +297,7 @@ class UpgradeSpec
     "that action with the upgraded launcher" ignore {
       prepareDistribution(
         portable        = true,
-        launcherVersion = Some(SemVer.of(0, 0, 2))
+        launcherVersion = Some(SemVer.of(1, 0, 2))
       )
       val enginesPath = getTestDirectory / "enso" / "dist"
       Files.createDirectories(enginesPath)
@@ -303,7 +306,7 @@ class UpgradeSpec
       //  engine distribution can be used in the test
 //      FileSystem.copyDirectory(
 //        Path.of("target/distribution/"),
-//        enginesPath / "0.1.0"
+//        enginesPath / "1.0.2"
 //      )
       val script  = getTestDirectory / "script.enso"
       val message = "Hello from test"
@@ -321,17 +324,20 @@ class UpgradeSpec
           script.toAbsolutePath.toString,
           "--use-system-jvm",
           "--use-enso-version",
-          "0.1.0"
+          "1.0.2"
         )
       )
-      result should returnSuccess
-      result.stdout should include(message)
+
+      withClue(result) {
+        result should returnSuccess
+        result.stdout should include(message)
+      }
     }
 
     "fail if another upgrade is running in parallel" taggedAs Flaky in {
       prepareDistribution(
         portable        = true,
-        launcherVersion = Some(SemVer.of(0, 0, 1))
+        launcherVersion = Some(SemVer.of(1, 0, 1))
       )
 
       val syncLocker = new FileLockManager(getTestDirectory / "enso" / "lock")
@@ -341,14 +347,14 @@ class UpgradeSpec
       // so acquiring this exclusive lock will stall access to that file until
       // the exclusive lock is released
       val lock = syncLocker.acquireLock(
-        "testasset-" + launcherManifestAssetName,
+        FakeAsset.lockNameForAsset(launcherManifestAssetName),
         LockType.Exclusive
       )
 
       val firstSuspended = startLauncher(
         Seq(
           "upgrade",
-          "0.0.2",
+          "1.0.2",
           "--internal-emulate-repository-wait",
           "--launcher-log-level=trace"
         )
@@ -361,7 +367,7 @@ class UpgradeSpec
 
         val secondFailed = run(Seq("upgrade", "0.0.0"))
 
-        secondFailed.stderr should include("Another upgrade is in progress")
+        secondFailed.stdout should include("Another upgrade is in progress")
         secondFailed.exitCode shouldEqual 1
       } catch {
         case e: TimeoutException =>
@@ -376,8 +382,37 @@ class UpgradeSpec
         lock.release()
       }
 
-      firstSuspended.join(timeoutSeconds = 20) should returnSuccess
-      checkVersion() shouldEqual SemVer.of(0, 0, 2)
+      firstSuspended.join(timeoutSeconds = 60) should returnSuccess
+      checkVersion() shouldEqual SemVer.of(1, 0, 2)
+    }
+
+    "should return a useful error message if upgrade cannot be performed because no upgrade path exists" taggedAs Flaky in {
+      prepareDistribution(
+        portable        = true,
+        launcherVersion = Some(SemVer.of(0, 0, 0))
+      )
+
+      val result = run(Seq("upgrade", "1.0.4"))
+      withClue(result) {
+        result.exitCode shouldEqual 1
+        result.stdout should include(
+          "no upgrade path has been found from the current version 0.0.0."
+        )
+      }
+    }
+
+    "should allow to upgrade the development version ignoring the version check, but warn about it" taggedAs Flaky in {
+      prepareDistribution(
+        portable        = true,
+        launcherVersion = Some(SemVer.of(0, 0, 0, "dev"))
+      )
+
+      val result = run(Seq("upgrade", "1.0.4"))
+      result should returnSuccess
+      withClue(result) {
+        result.stdout should include("development version")
+        result.stdout should include("minimum version check can be ignored")
+      }
     }
   }
 }
diff --git a/lib/rust/launcher-shims/src/bin/launcher_000dev.rs b/lib/rust/launcher-shims/src/bin/launcher_000dev.rs
new file mode 100644
index 0000000000..45aa3af97a
--- /dev/null
+++ b/lib/rust/launcher-shims/src/bin/launcher_000dev.rs
@@ -0,0 +1,12 @@
+use launcher_shims::wrap_launcher;
+
+
+
+// ===========================
+// === EntryPoint0.0.0-dev ===
+// ===========================
+
+/// Runs the launcher wrapper overriding the version to 0.0.0-dev.
+fn main() {
+    wrap_launcher("0.0.0-dev")
+}
diff --git a/lib/rust/launcher-shims/src/bin/launcher_001.rs b/lib/rust/launcher-shims/src/bin/launcher_001.rs
deleted file mode 100644
index 7c4ae461d6..0000000000
--- a/lib/rust/launcher-shims/src/bin/launcher_001.rs
+++ /dev/null
@@ -1,12 +0,0 @@
-use launcher_shims::wrap_launcher;
-
-
-
-// =======================
-// === EntryPoint0.0.1 ===
-// =======================
-
-/// Runs the launcher wrapper overriding the version to 0.0.1.
-fn main() {
-    wrap_launcher("0.0.1")
-}
diff --git a/lib/rust/launcher-shims/src/bin/launcher_002.rs b/lib/rust/launcher-shims/src/bin/launcher_002.rs
deleted file mode 100644
index 493a4b185c..0000000000
--- a/lib/rust/launcher-shims/src/bin/launcher_002.rs
+++ /dev/null
@@ -1,12 +0,0 @@
-use launcher_shims::wrap_launcher;
-
-
-
-// =======================
-// === EntryPoint0.0.2 ===
-// =======================
-
-/// Runs the launcher wrapper overriding the version to 0.0.2.
-fn main() {
-    wrap_launcher("0.0.2")
-}
diff --git a/lib/rust/launcher-shims/src/bin/launcher_003.rs b/lib/rust/launcher-shims/src/bin/launcher_003.rs
deleted file mode 100644
index 3e1f9983f8..0000000000
--- a/lib/rust/launcher-shims/src/bin/launcher_003.rs
+++ /dev/null
@@ -1,12 +0,0 @@
-use launcher_shims::wrap_launcher;
-
-
-
-// =======================
-// === EntryPoint0.0.3 ===
-// =======================
-
-/// Runs the launcher wrapper overriding the version to 0.0.3.
-fn main() {
-    wrap_launcher("0.0.3")
-}
diff --git a/lib/rust/launcher-shims/src/bin/launcher_004.rs b/lib/rust/launcher-shims/src/bin/launcher_004.rs
deleted file mode 100644
index 50244ed03d..0000000000
--- a/lib/rust/launcher-shims/src/bin/launcher_004.rs
+++ /dev/null
@@ -1,12 +0,0 @@
-use launcher_shims::wrap_launcher;
-
-
-
-// =======================
-// === EntryPoint0.0.4 ===
-// =======================
-
-/// Runs the launcher wrapper overriding the version to 0.0.4.
-fn main() {
-    wrap_launcher("0.0.4")
-}
diff --git a/lib/rust/launcher-shims/src/bin/launcher_101.rs b/lib/rust/launcher-shims/src/bin/launcher_101.rs
new file mode 100644
index 0000000000..de9d0f69ce
--- /dev/null
+++ b/lib/rust/launcher-shims/src/bin/launcher_101.rs
@@ -0,0 +1,12 @@
+use launcher_shims::wrap_launcher;
+
+
+
+// =======================
+// === EntryPoint1.0.1 ===
+// =======================
+
+/// Runs the launcher wrapper overriding the version to 1.0.1.
+fn main() {
+    wrap_launcher("1.0.1")
+}
diff --git a/lib/rust/launcher-shims/src/bin/launcher_102.rs b/lib/rust/launcher-shims/src/bin/launcher_102.rs
new file mode 100644
index 0000000000..69afd5c232
--- /dev/null
+++ b/lib/rust/launcher-shims/src/bin/launcher_102.rs
@@ -0,0 +1,12 @@
+use launcher_shims::wrap_launcher;
+
+
+
+// =======================
+// === EntryPoint1.0.2 ===
+// =======================
+
+/// Runs the launcher wrapper overriding the version to 1.0.2.
+fn main() {
+    wrap_launcher("1.0.2")
+}
diff --git a/lib/rust/launcher-shims/src/bin/launcher_103.rs b/lib/rust/launcher-shims/src/bin/launcher_103.rs
new file mode 100644
index 0000000000..bf44350c14
--- /dev/null
+++ b/lib/rust/launcher-shims/src/bin/launcher_103.rs
@@ -0,0 +1,12 @@
+use launcher_shims::wrap_launcher;
+
+
+
+// =======================
+// === EntryPoint1.0.3 ===
+// =======================
+
+/// Runs the launcher wrapper overriding the version to 1.0.3.
+fn main() {
+    wrap_launcher("1.0.3")
+}
diff --git a/lib/rust/launcher-shims/src/bin/launcher_104.rs b/lib/rust/launcher-shims/src/bin/launcher_104.rs
new file mode 100644
index 0000000000..f376104d04
--- /dev/null
+++ b/lib/rust/launcher-shims/src/bin/launcher_104.rs
@@ -0,0 +1,12 @@
+use launcher_shims::wrap_launcher;
+
+
+
+// =======================
+// === EntryPoint1.0.4 ===
+// =======================
+
+/// Runs the launcher wrapper overriding the version to 1.0.4.
+fn main() {
+    wrap_launcher("1.0.4")
+}
diff --git a/lib/rust/launcher-shims/src/bin/launcher_9999990.rs b/lib/rust/launcher-shims/src/bin/launcher_9999990.rs
new file mode 100644
index 0000000000..57f46f1be1
--- /dev/null
+++ b/lib/rust/launcher-shims/src/bin/launcher_9999990.rs
@@ -0,0 +1,12 @@
+use launcher_shims::wrap_launcher;
+
+
+
+// ===========================
+// === EntryPoint99.9999.0 ===
+// ===========================
+
+/// Runs the launcher wrapper overriding the version to 99.9999.0.
+fn main() {
+    wrap_launcher("99.9999.0")
+}
diff --git a/lib/rust/launcher-shims/src/lib.rs b/lib/rust/launcher-shims/src/lib.rs
index a4088a921e..85cd7dcbfe 100644
--- a/lib/rust/launcher-shims/src/lib.rs
+++ b/lib/rust/launcher-shims/src/lib.rs
@@ -74,7 +74,7 @@ pub fn wrap_launcher(version: impl AsRef<str>) {
 
 /// Appends a line to the file located at the provided path.
 pub fn append_to_log(path: PathBuf, line: impl AsRef<str>) -> io::Result<()> {
-    let mut log_file = OpenOptions::new().append(true).open(path)?;
+    let mut log_file = OpenOptions::new().create(true).append(true).open(path)?;
     writeln!(log_file, "{}", line.as_ref())?;
     Ok(())
 }
diff --git a/lib/scala/cli/src/main/scala/org/enso/cli/task/MappedTask.scala b/lib/scala/cli/src/main/scala/org/enso/cli/task/MappedTask.scala
index 15e1508ec5..81ca6eb210 100644
--- a/lib/scala/cli/src/main/scala/org/enso/cli/task/MappedTask.scala
+++ b/lib/scala/cli/src/main/scala/org/enso/cli/task/MappedTask.scala
@@ -6,7 +6,7 @@ import scala.util.Try
   *
   * Used internally by [[TaskProgress.flatMap]].
   */
-private class MappedTask[A, B](source: TaskProgress[A], f: A => Try[B])
+private class MappedTask[A, B](source: TaskProgress[A], f: Try[A] => Try[B])
     extends TaskProgress[B] { self =>
 
   var listeners: List[ProgressListener[B]] = Nil
@@ -17,7 +17,7 @@ private class MappedTask[A, B](source: TaskProgress[A], f: A => Try[B])
       listeners.foreach(_.progressUpdate(done, total))
 
     override def done(result: Try[A]): Unit = self.synchronized {
-      val mapped = result.flatMap(f)
+      val mapped = f(result)
       savedResult = Some(mapped)
       listeners.foreach(_.done(mapped))
     }
diff --git a/lib/scala/cli/src/main/scala/org/enso/cli/task/TaskProgress.scala b/lib/scala/cli/src/main/scala/org/enso/cli/task/TaskProgress.scala
index 87e6b6354f..88b336f328 100644
--- a/lib/scala/cli/src/main/scala/org/enso/cli/task/TaskProgress.scala
+++ b/lib/scala/cli/src/main/scala/org/enso/cli/task/TaskProgress.scala
@@ -50,7 +50,19 @@ trait TaskProgress[A] {
     *         succeeded and the transformation succeeded too
     */
   def flatMap[B](f: A => Try[B]): TaskProgress[B] =
-    new MappedTask(this, f)
+    new MappedTask(this, (t: Try[A]) => t.flatMap(f))
+
+  /** Alters the task by transforming its failure case with a partial function
+    * `pf`.
+    *
+    * @param pf the partial function that can transform the original error
+    * @tparam B resulting type of `pf`
+    * @return a new [[TaskProgress]] with update failure behaviours
+    */
+  def recoverWith[B >: A](
+    pf: PartialFunction[Throwable, Try[B]]
+  ): TaskProgress[B] =
+    new MappedTask(this, (t: Try[A]) => t.recoverWith(pf))
 
   /** Alters the task by transforming its result with a function `f`.
     *
diff --git a/lib/scala/downloader/src/main/scala/org/enso/downloader/http/HTTPDownload.scala b/lib/scala/downloader/src/main/scala/org/enso/downloader/http/HTTPDownload.scala
index a3a3af6330..3d1966891d 100644
--- a/lib/scala/downloader/src/main/scala/org/enso/downloader/http/HTTPDownload.scala
+++ b/lib/scala/downloader/src/main/scala/org/enso/downloader/http/HTTPDownload.scala
@@ -44,7 +44,7 @@ object HTTPDownload {
     sizeHint: Option[Long] = None,
     encoding: Charset      = StandardCharsets.UTF_8
   ): TaskProgress[APIResponse] = {
-    logger.debug("Fetching [{}].", request.requestImpl.uri())
+    logger.debug("Fetching [{} {}].", request.method, request.uri)
     val taskProgress =
       new TaskProgressImplementation[APIResponse](ProgressUnit.Bytes)
     val total: java.lang.Long = if (sizeHint.isDefined) sizeHint.get else null
diff --git a/lib/scala/downloader/src/main/scala/org/enso/downloader/http/HTTPRequest.scala b/lib/scala/downloader/src/main/scala/org/enso/downloader/http/HTTPRequest.scala
index 9427ca34e1..164e165d33 100644
--- a/lib/scala/downloader/src/main/scala/org/enso/downloader/http/HTTPRequest.scala
+++ b/lib/scala/downloader/src/main/scala/org/enso/downloader/http/HTTPRequest.scala
@@ -5,4 +5,11 @@ import java.net.http.HttpRequest
 /** Wraps an underlying HTTP request implementation to make the outside API
   * independent of the internal implementation.
   */
-case class HTTPRequest(requestImpl: HttpRequest)
+case class HTTPRequest(requestImpl: HttpRequest) {
+
+  /** Returns the method of this request. */
+  def method: String = requestImpl.method()
+
+  /** Returns the URI of this request as string, used e.g. for logging. */
+  def uri: String = requestImpl.uri().toString
+}
diff --git a/lib/scala/runtime-version-manager/src/main/java/org/enso/runtimeversionmanager/releases/testing/CompressZipArchive.java b/lib/scala/runtime-version-manager/src/main/java/org/enso/runtimeversionmanager/releases/testing/CompressZipArchive.java
new file mode 100644
index 0000000000..3b8ff6ce1a
--- /dev/null
+++ b/lib/scala/runtime-version-manager/src/main/java/org/enso/runtimeversionmanager/releases/testing/CompressZipArchive.java
@@ -0,0 +1,30 @@
+package org.enso.runtimeversionmanager.releases.testing;
+
+import java.io.IOException;
+import java.io.UncheckedIOException;
+import java.nio.file.Files;
+import java.nio.file.Path;
+import java.util.zip.ZipEntry;
+import java.util.zip.ZipOutputStream;
+
+class CompressZipArchive {
+  static void compress(Path source, Path destination) throws IOException {
+    try (var zip = Files.newOutputStream(destination);
+        var zos = new ZipOutputStream(zip);
+        var files = Files.walk(source)) {
+      files
+          .filter(path -> !Files.isDirectory(path))
+          .forEach(
+              path -> {
+                var zipEntry = new ZipEntry(source.relativize(path).toString());
+                try {
+                  zos.putNextEntry(zipEntry);
+                  Files.copy(path, zos);
+                  zos.closeEntry();
+                } catch (IOException e) {
+                  throw new UncheckedIOException(e);
+                }
+              });
+    }
+  }
+}
diff --git a/lib/scala/runtime-version-manager/src/main/scala/org/enso/runtimeversionmanager/releases/ReleaseProviderException.scala b/lib/scala/runtime-version-manager/src/main/scala/org/enso/runtimeversionmanager/releases/ReleaseProviderException.scala
index 34eccc58dd..ae7470eb30 100644
--- a/lib/scala/runtime-version-manager/src/main/scala/org/enso/runtimeversionmanager/releases/ReleaseProviderException.scala
+++ b/lib/scala/runtime-version-manager/src/main/scala/org/enso/runtimeversionmanager/releases/ReleaseProviderException.scala
@@ -1,5 +1,7 @@
 package org.enso.runtimeversionmanager.releases
 
+import org.enso.downloader.http.ResourceNotFound
+
 /** Indicates a release provider failure. */
 sealed class ReleaseProviderException(message: String, cause: Throwable)
     extends RuntimeException(message, cause) {
@@ -30,6 +32,20 @@ case class ReleaseNotFound(
   message: Option[String] = None,
   cause: Throwable        = null
 ) extends ReleaseProviderException(
-      message.getOrElse(s"Cannot find release `$tag`."),
+      ReleaseNotFound.constructMessage(tag, message, cause),
       cause
     )
+
+object ReleaseNotFound {
+  private def constructMessage(
+    tag: String,
+    message: Option[String],
+    cause: Throwable
+  ): String =
+    message.getOrElse {
+      val isCauseInteresting = cause != null && cause != ResourceNotFound()
+      val suffix =
+        if (isCauseInteresting) s" Caused by: ${cause.getMessage}" else ""
+      s"Cannot find release `$tag`.$suffix"
+    }
+}
diff --git a/lib/scala/runtime-version-manager/src/main/scala/org/enso/runtimeversionmanager/releases/github/GithubAPI.scala b/lib/scala/runtime-version-manager/src/main/scala/org/enso/runtimeversionmanager/releases/github/GithubAPI.scala
index 2d4babd9df..4cea85ed0d 100644
--- a/lib/scala/runtime-version-manager/src/main/scala/org/enso/runtimeversionmanager/releases/github/GithubAPI.scala
+++ b/lib/scala/runtime-version-manager/src/main/scala/org/enso/runtimeversionmanager/releases/github/GithubAPI.scala
@@ -1,5 +1,7 @@
 package org.enso.runtimeversionmanager.releases.github
 
+import com.typesafe.scalalogging.Logger
+
 import java.nio.file.Path
 import io.circe._
 import io.circe.parser._
@@ -7,6 +9,7 @@ import org.enso.cli.task.TaskProgress
 import org.enso.downloader.http.{
   APIResponse,
   HTTPDownload,
+  HTTPException,
   HTTPRequestBuilder,
   Header,
   URIBuilder
@@ -16,7 +19,7 @@ import org.enso.runtimeversionmanager.releases.{
   ReleaseProviderException
 }
 
-import scala.util.{Success, Try}
+import scala.util.{Failure, Success, Try}
 
 /** Contains functions used to query the GitHubAPI endpoints.
   */
@@ -61,13 +64,31 @@ object GithubAPI {
     * bar for this task.
     */
   def listReleases(repository: Repository): Try[Seq[Release]] = {
+    releaseListCache.get(repository) match {
+      case Some(cachedList) =>
+        logger.debug("Using cached release list for repository {}", repository)
+        Success(cachedList)
+      case None =>
+        makeListReleasesRequest(repository).map { releases =>
+          releaseListCache.put(repository, releases)
+          releases
+        }
+    }
+  }
+
+  private def makeListReleasesRequest(
+    repository: Repository
+  ): Try[Seq[Release]] = {
     val perPage = 100
     def listPage(page: Int): Try[Seq[Release]] = {
-      val uri = (projectURI(repository) / "releases") ?
-        ("per_page" -> perPage.toString) ? ("page" -> page.toString)
+      val uri =
+        ((projectURI(
+          repository
+        ) / "releases") ? ("per_page" -> perPage.toString) ? ("page" -> page.toString))
+          .build()
 
       val downloadTask = HTTPDownload
-        .fetchString(HTTPRequestBuilder.fromURI(uri.build()).GET)
+        .fetchString(HTTPRequestBuilder.fromURI(uri).GET)
         .flatMap(response =>
           parse(response.content)
             .flatMap(
@@ -95,13 +116,47 @@ object GithubAPI {
     listAllPages(1)
   }
 
+  /** Fetching the list of releases may involve making multiple requests with big payloads, so it is good to cache the relevant information extracted from it to avoid unnecessary re-fetching.
+    *
+    * The runtime version manager assumes that the list of known releases will not change during the runtime of the program, so the cache is never invalidated as long as the program is running.
+    */
+  private val releaseListCache
+    : collection.concurrent.TrieMap[Repository, Seq[Release]] =
+    collection.concurrent.TrieMap.empty
+
   /** Fetches release metadata for the release associated with the given tag.
     */
   def getRelease(repo: Repository, tag: String): TaskProgress[Release] = {
-    val uri = projectURI(repo) / "releases" / "tags" / tag
+    findCachedRelease(repo, tag) match {
+      case Some(release) =>
+        logger.debug(
+          "Using cached release for tag {} in repository {}",
+          tag,
+          repo
+        )
+        TaskProgress.runImmediately(release)
+      case None =>
+        makeGetSingleReleaseRequest(repo, tag)
+    }
+  }
+
+  private def findCachedRelease(
+    repo: Repository,
+    tag: String
+  ): Option[Release] =
+    for {
+      cachedList <- releaseListCache.get(repo)
+      release    <- cachedList.find(_.tag == tag)
+    } yield release
+
+  private def makeGetSingleReleaseRequest(
+    repo: Repository,
+    tag: String
+  ): TaskProgress[Release] = {
+    val uri = (projectURI(repo) / "releases" / "tags" / tag).build()
 
     HTTPDownload
-      .fetchString(HTTPRequestBuilder.fromURI(uri.build()).GET)
+      .fetchString(HTTPRequestBuilder.fromURI(uri).GET)
       .flatMap(response =>
         parse(response.content)
           .flatMap(_.as[Release])
@@ -114,6 +169,9 @@ object GithubAPI {
           )
           .toTry
       )
+      .recoverWith { case httpException: HTTPException =>
+        Failure(ReleaseNotFound(tag, cause = httpException))
+      }
   }
 
   /** A helper function that detecte a rate-limit error and tries to make a more
@@ -165,6 +223,7 @@ object GithubAPI {
       .addHeader("Accept", "application/octet-stream")
       .GET
 
+    System.err.println(s"Preparing to download asset ${asset.url}")
     HTTPDownload
       .download(request, destination, Some(asset.size))
       .map(_ => ())
@@ -189,4 +248,6 @@ object GithubAPI {
       assets <- json.get[Seq[Asset]]("assets")
     } yield Release(tag, assets)
   }
+
+  private val logger: Logger = Logger[GithubAPI.type]
 }
diff --git a/lib/scala/runtime-version-manager/src/main/scala/org/enso/runtimeversionmanager/releases/testing/FakeReleaseProvider.scala b/lib/scala/runtime-version-manager/src/main/scala/org/enso/runtimeversionmanager/releases/testing/FakeReleaseProvider.scala
index 96df4cff4e..2d9fe0b23b 100644
--- a/lib/scala/runtime-version-manager/src/main/scala/org/enso/runtimeversionmanager/releases/testing/FakeReleaseProvider.scala
+++ b/lib/scala/runtime-version-manager/src/main/scala/org/enso/runtimeversionmanager/releases/testing/FakeReleaseProvider.scala
@@ -118,7 +118,7 @@ case class FakeAsset(
     */
   private def maybeWaitForAsset(): Unit =
     lockManagerForAssets.foreach { lockManager =>
-      val name     = "testasset-" + fileName
+      val name     = FakeAsset.lockNameForAsset(fileName)
       val lockType = LockType.Shared
       val lock = lockManager.tryAcquireLock(
         name,
@@ -186,3 +186,9 @@ case class FakeAsset(
       }
     }
 }
+
+object FakeAsset {
+
+  /** Name for the lock used for synchronizing access to asset, used when instrumenting tests. */
+  def lockNameForAsset(assetName: String): String = s"testasset-$assetName"
+}
diff --git a/lib/scala/runtime-version-manager/src/main/scala/org/enso/runtimeversionmanager/releases/testing/TestArchivePackager.scala b/lib/scala/runtime-version-manager/src/main/scala/org/enso/runtimeversionmanager/releases/testing/TestArchivePackager.scala
index 7f75e9f857..a9a77b1c32 100644
--- a/lib/scala/runtime-version-manager/src/main/scala/org/enso/runtimeversionmanager/releases/testing/TestArchivePackager.scala
+++ b/lib/scala/runtime-version-manager/src/main/scala/org/enso/runtimeversionmanager/releases/testing/TestArchivePackager.scala
@@ -53,22 +53,6 @@ object TestArchivePackager {
   }
 
   private def packZip(source: Path, destination: Path): Unit = {
-    val files = FileSystem.listDirectory(source)
-    val exitCode = Process(
-      Seq(
-        "powershell",
-        "Compress-Archive",
-        "-Path",
-        files.map(_.getFileName.toString).mkString(","),
-        "-DestinationPath",
-        destination.toAbsolutePath.toString
-      ),
-      source.toFile
-    ).!
-    if (exitCode != 0) {
-      throw new RuntimeException(
-        s"tar failed. Cannot create fake-archive for $source"
-      )
-    }
+    CompressZipArchive.compress(source, destination)
   }
 }
diff --git a/project/NativeImage.scala b/project/NativeImage.scala
index d3f39c4197..3ffbf5ec5c 100644
--- a/project/NativeImage.scala
+++ b/project/NativeImage.scala
@@ -97,7 +97,7 @@ object NativeImage {
   ): Def.Initialize[Task[Unit]] = Def
     .task {
       val log       = state.value.log
-      val targetLoc = artifactFile(targetDir, name, false)
+      val targetLoc = artifactFile(targetDir, name, withExtension = false)
 
       def nativeImagePath(prefix: Path)(path: Path): Path = {
         val base = path.resolve(prefix)
@@ -253,7 +253,7 @@ object NativeImage {
         s"Started building $targetLoc native image. The output is captured."
       )
       val retCode    = process.!(processLogger)
-      val targetFile = artifactFile(targetDir, name, true)
+      val targetFile = artifactFile(targetDir, name)
       if (retCode != 0 || !targetFile.exists()) {
         log.error(s"Native Image build of $targetFile failed, with output: ")
         println(sb.toString())
@@ -318,7 +318,7 @@ object NativeImage {
   def artifactFile(
     targetDir: File,
     name: String,
-    withExtension: Boolean = false
+    withExtension: Boolean = true
   ): File = {
     val artifactName =
       if (withExtension && Platform.isWindows) name + ".exe"