diff --git a/tests/slow-activation/delay-activation.nix b/tests/slow-activation/delay-activation.nix
new file mode 100644
index 00000000..6fbdfb66
--- /dev/null
+++ b/tests/slow-activation/delay-activation.nix
@@ -0,0 +1,14 @@
+{ pkgs, lib, ... }:
+
+{
+  imports = [
+    <nixos-wsl/modules>
+  ];
+
+  wsl.enable = true;
+
+  system.activationScripts."00-delay" = ''
+    echo "Delaying activation for 15 seconds..."
+    sleep 15s
+  '';
+}
diff --git a/tests/slow-activation/slow-activation.Tests.ps1 b/tests/slow-activation/slow-activation.Tests.ps1
new file mode 100644
index 00000000..f6caaf94
--- /dev/null
+++ b/tests/slow-activation/slow-activation.Tests.ps1
@@ -0,0 +1,22 @@
+BeforeAll {
+  . $PSScriptRoot/../lib/lib.ps1
+}
+
+Describe "Slow Activation Script" {
+  BeforeAll {
+    $distro = [Distro]::new()
+  }
+
+  It "should not cause starting a shell to fail" {
+    $distro.InstallConfig("$PSScriptRoot/delay-activation.nix", "boot")
+    $distro.Shutdown()
+
+    $distro.Launch("echo 'TEST'") | Select-Object -Last 1 | Tee-Object -Variable output
+    $output | Should -BeExactly "TEST"
+    $LASTEXITCODE | Should -Be 0
+  }
+
+  AfterAll {
+    $distro.Uninstall()
+  }
+}
diff --git a/utils/Cargo.toml b/utils/Cargo.toml
index 2a170680..1db16223 100644
--- a/utils/Cargo.toml
+++ b/utils/Cargo.toml
@@ -7,7 +7,7 @@ rust-version = "1.69.0"
 
 [dependencies]
 anyhow = { version = "1.0.82", features = ["backtrace"] }
-nix = { version = "0.29.0", features = ["mount", "process"] }
+nix = { version = "0.29.0", features = ["mount", "process", "user", "inotify"] }
 log = "0.4.21"
 kernlog = "0.3.1"
 systemd-journal-logger = "2.1.1"
diff --git a/utils/src/shell_wrapper.rs b/utils/src/shell_wrapper.rs
index 5bfdb73a..b259ccbe 100644
--- a/utils/src/shell_wrapper.rs
+++ b/utils/src/shell_wrapper.rs
@@ -1,8 +1,10 @@
 use anyhow::{anyhow, Context};
 use log::{error, info, warn, LevelFilter};
 use nix::libc::{sigaction, PT_NULL, SIGCHLD, SIG_IGN};
+use nix::sys::inotify::{AddWatchFlags, InitFlags, Inotify};
 use std::mem::MaybeUninit;
 use std::os::unix::process::CommandExt;
+use std::path::Path;
 use std::process::Command;
 use std::{env, fs::read_link};
 use systemd_journal_logger::JournalLog;
@@ -17,6 +19,28 @@ fn real_main() -> anyhow::Result<()> {
     // Therefore we dereference our symlink to get whatever it was originally.
     let shell = read_link(exe_dir.join("shell")).context("when locating the wrapped shell")?;
 
+    if shell.starts_with("/run/current-system/sw/bin/")
+        && !Path::new("/run/current-system").exists()
+    {
+        let inotify = Inotify::init(InitFlags::empty()).context("When initializing inotify")?;
+
+        // Watch changes in /run to re-check if the activation script has finished
+        let wd = inotify.add_watch("/run", AddWatchFlags::IN_CREATE).unwrap();
+
+        let mut warning = false;
+
+        // Check if the activation script has finished by now
+        while !Path::new("/run/current-system").exists() {
+            if (!warning) {
+                warning = true;
+                warn!("Activation script has not finished! Waiting for /run/current-system/sw/bin to exist");
+            }
+            let events = inotify
+                .read_events()
+                .context("When reading inotify events")?;
+        }
+    }
+
     // Set the SHELL environment variable to the wrapped shell instead of the wrapper
     let shell_env = env::var_os("SHELL");
     if shell_env == Some(exe.into()) {
@@ -112,7 +136,15 @@ fn main() {
                 .context("When installing journal logger")
         })
     {
-        warn!("Error while setting up journal logger: {:?}", err);
+        if nix::unistd::geteuid().is_root() {
+            // Journal isn't available during early boot. Try to use kmsg instead
+            if let Err(err) = kernlog::init().context("When initializing kernel logger") {
+                warn!("Error while setting up kernel logger: {:?}", err);
+            }
+        } else {
+            // Users can't access the kernel log
+            warn!("Error while setting up journal logger: {:?}", err);
+        }
     }
 
     log::set_max_level(LevelFilter::Info);