diff --git a/src/pane.rs b/src/pane.rs
index 9fcddce0..1dd641f4 100644
--- a/src/pane.rs
+++ b/src/pane.rs
@@ -14,7 +14,9 @@ use ratatui::{layout::Rect, Frame};
 #[cfg(test)]
 use tokio::sync::watch;
 use tokio::sync::{mpsc, Notify};
-use tracing::{debug, error, info, warn};
+#[cfg(not(windows))]
+use tracing::debug;
+use tracing::{error, info, warn};
 
 use crate::detect::{Agent, AgentState};
 use crate::events::AppEvent;
diff --git a/website/install.ps1 b/website/install.ps1
index 65192108..66f9a8c9 100644
--- a/website/install.ps1
+++ b/website/install.ps1
@@ -196,7 +196,8 @@ function Set-ManagedJunction {
     param(
         [string]$LinkPath,
         [string]$TargetPath,
-        [string]$ManagedTargetPrefix
+        [string]$ManagedTargetPrefix,
+        [bool]$AllowLegacyHerdrBinMigration = $false
     )
 
     if (Test-Path -LiteralPath $LinkPath) {
@@ -215,9 +216,12 @@ function Set-ManagedJunction {
             Remove-Item -LiteralPath $LinkPath -Force
         } elseif ($item.PSIsContainer) {
             if ((Get-ChildItem -LiteralPath $LinkPath -Force | Select-Object -First 1) -ne $null) {
-                throw "Refusing to replace non-empty directory at $LinkPath with a junction."
+                if (-not (Move-LegacyHerdrBinDirectory -Path $LinkPath -AllowMigration $AllowLegacyHerdrBinMigration)) {
+                    throw "Refusing to replace non-empty directory at $LinkPath with a junction."
+                }
+            } else {
+                Remove-Item -LiteralPath $LinkPath -Force
             }
-            Remove-Item -LiteralPath $LinkPath -Force
         } else {
             throw "Refusing to replace file at $LinkPath with a junction."
         }
@@ -227,6 +231,27 @@ function Set-ManagedJunction {
     New-Item -ItemType Junction -Path $LinkPath -Target $TargetPath | Out-Null
 }
 
+function Move-LegacyHerdrBinDirectory {
+    param(
+        [string]$Path,
+        [bool]$AllowMigration
+    )
+
+    if (-not $AllowMigration) {
+        return $false
+    }
+
+    $entries = @(Get-ChildItem -LiteralPath $Path -Force)
+    if ($entries.Count -ne 1 -or $entries[0].PSIsContainer -or $entries[0].Name -ine "herdr.exe") {
+        return $false
+    }
+
+    $legacyPath = "$Path.legacy.$([System.Guid]::NewGuid().ToString("N"))"
+    Move-Item -LiteralPath $Path -Destination $legacyPath
+    Write-Step "Moved legacy Herdr bin directory to $legacyPath."
+    return $true
+}
+
 function Remove-StaleInstallArtifacts {
     param([string]$ReleasesDir)
 
@@ -396,6 +421,15 @@ $visibleBinDir = if ([string]::IsNullOrWhiteSpace($InstallDir)) {
 } else {
     $InstallDir
 }
+$allowLegacyVisibleBinMigration = $false
+try {
+    $allowLegacyVisibleBinMigration = [System.IO.Path]::GetFullPath($visibleBinDir).TrimEnd("\").Equals(
+        [System.IO.Path]::GetFullPath($defaultVisibleBinDir).TrimEnd("\"),
+        [System.StringComparison]::OrdinalIgnoreCase
+    )
+} catch {
+    $allowLegacyVisibleBinMigration = $false
+}
 
 $existingHerdr = Get-HerdrCommandSource
 if (-not [string]::IsNullOrWhiteSpace($existingHerdr) -and -not (Test-PathStartsWith -Path $existingHerdr -Prefix $visibleBinDir)) {
@@ -436,7 +470,7 @@ try {
         }
 
         Set-ManagedJunction -LinkPath $currentDir -TargetPath $releaseDir -ManagedTargetPrefix $releasesDir
-        Set-ManagedJunction -LinkPath $visibleBinDir -TargetPath $releaseDir -ManagedTargetPrefix $standaloneRoot
+        Set-ManagedJunction -LinkPath $visibleBinDir -TargetPath $releaseDir -ManagedTargetPrefix $standaloneRoot -AllowLegacyHerdrBinMigration $allowLegacyVisibleBinMigration
 
         $herdrCommand = Join-Path $visibleBinDir "herdr.exe"
         & $herdrCommand --version *> $null