diff --git a/Makefile b/Makefile
index 4d2b2fa..d02815e 100644
--- a/Makefile
+++ b/Makefile
@@ -13,12 +13,15 @@ all: .version install.exe
 
 .version:
 	sed 's|!define VERSION||g' src/nsis/i2pbrowser-version.nsi | sed 's| |=|g' > .version
-	make version.txt
+	make version.txt src/nsis/i2pbrowser_jpackage.nsi
 
 version.txt:
 	echo "$(PROFILE_VERSION)" > src/profile/version.txt
 	echo "$(PROFILE_VERSION)" > src/app-profile/version.txt
 
+src/nsis/i2pbrowser_jpackage.nsi:
+	echo "!define I2P_VERSION $(I2P_VERSION)" > src/nsis/i2pbrowser_jpackage.nsi
+
 jpackage: .version I2P all
 
 help: .version
diff --git a/java/net/i2p/router/WinUpdateProcess.java b/java/net/i2p/router/WinUpdateProcess.java
index 5dfa30b..3c060bc 100644
--- a/java/net/i2p/router/WinUpdateProcess.java
+++ b/java/net/i2p/router/WinUpdateProcess.java
@@ -11,17 +11,34 @@ class WinUpdateProcess implements Runnable {
     private final Log _log = I2PAppContext.getGlobalContext().logManager().getLog(WinUpdateProcess.class);
     private final RouterContext ctx;
     private final Supplier<String> versionSupplier;
-    private final File file = null;
+    private final File file;
     
     WinUpdateProcess(RouterContext ctx, Supplier<String> versionSupplier, File file) {
         this.ctx = ctx;
         this.versionSupplier = versionSupplier;
+        this.file = file;
     }
 
     private void runUpdateInstaller(File file){
-        ProcessBuilder pb = new ProcessBuilder("cmd", "/c", file.getAbsolutePath(), "/S");
+        String version = versionSupplier.get();
+
+        var workingDir = new File(ctx.getConfigDir(), "mac_updates");
+        var logFile = new File(workingDir, "log-" + version + ".txt");
+
+        ProcessBuilder pb = new ProcessBuilder(file.getAbsolutePath());
+        var env = pb.environment();
+        env.put("OLD_I2P_VERSION", version);
+        env.remove("RESTART_I2P");
+
+        int exitCode = ctx.router().scheduledGracefulExitCode();
+        if (exitCode == Router.EXIT_HARD_RESTART || exitCode == Router.EXIT_GRACEFUL_RESTART)
+            env.put("RESTART_I2P", "true");
+
         try {
-            pb.start();
+            pb.directory(workingDir).
+                redirectErrorStream(true).
+                redirectOutput(logFile).
+                start();
         } catch (IOException ex) {
             if (_log.shouldWarn())
                 _log.warn("Unable to run update-program in background. Update will fail.");
diff --git a/src/nsis/i2pbrowser-installer.nsi b/src/nsis/i2pbrowser-installer.nsi
index ff083cc..01bcdde 100644
--- a/src/nsis/i2pbrowser-installer.nsi
+++ b/src/nsis/i2pbrowser-installer.nsi
@@ -11,6 +11,7 @@ UniCode true
 !define CONSOLE_URL "http://127.0.0.1:7657/home"
 
 !include i2pbrowser-version.nsi
+!include i2pbrowser-jpackage.nsi
 !include FindProcess.nsh
 
 var FFINSTEXE
@@ -242,25 +243,53 @@ Section Install
     ${If} ${FileExists} "$I2PINSTEXE\jpackaged"
         createDirectory $I2PINSTEXE
         SetOutPath $I2PINSTEXE
-        File /nonfatal /a /r "I2P\"
-        File /nonfatal "I2P\config\jpackaged"
 
-        createDirectory "$I2PINSTEXE\"
-        SetOutPath "$I2PINSTEXE\"
+        ${If} ${Silent}
+          ReadEnvStr $0 OLD_I2P_VERSION
+          ${If} $0 < ${I2P_VERSION}
+            File /nonfatal /a /r "I2P\"
+            File /nonfatal "I2P\config\jpackaged"
 
-        createDirectory "$I2PINSTEXE\webapps\"
-        SetOutPath "$I2PINSTEXE\webapps\"
-        File /nonfatal /a /r "I2P\config\webapps\"
+            createDirectory "$I2PINSTEXE\"
+            SetOutPath "$I2PINSTEXE\"
 
-        createDirectory "$I2PINSTEXE\geoip\"
-        SetOutPath "$I2PINSTEXE\geoip\"
-        File /nonfatal /a /r "I2P\config\geoip\"
+            createDirectory "$I2PINSTEXE\webapps\"
+            SetOutPath "$I2PINSTEXE\webapps\"
+            File /nonfatal /a /r "I2P\config\webapps\"
 
-        createDirectory "$I2PINSTEXE\certificates\"
-        SetOutPath "$I2PINSTEXE\certificates\"
-        File /nonfatal /a /r "I2P\config\certificates\"
+            createDirectory "$I2PINSTEXE\geoip\"
+            SetOutPath "$I2PINSTEXE\geoip\"
+            File /nonfatal /a /r "I2P\config\geoip\"
+
+            createDirectory "$I2PINSTEXE\certificates\"
+            SetOutPath "$I2PINSTEXE\certificates\"
+            File /nonfatal /a /r "I2P\config\certificates\"
+          ${EndIf}  
+        ${Else}
+          File /nonfatal /a /r "I2P\"
+          File /nonfatal "I2P\config\jpackaged"
+
+          createDirectory "$I2PINSTEXE\"
+          SetOutPath "$I2PINSTEXE\"
+
+          createDirectory "$I2PINSTEXE\webapps\"
+          SetOutPath "$I2PINSTEXE\webapps\"
+          File /nonfatal /a /r "I2P\config\webapps\"
+
+          createDirectory "$I2PINSTEXE\geoip\"
+          SetOutPath "$I2PINSTEXE\geoip\"
+          File /nonfatal /a /r "I2P\config\geoip\"
+
+          createDirectory "$I2PINSTEXE\certificates\"
+          SetOutPath "$I2PINSTEXE\certificates\"
+          File /nonfatal /a /r "I2P\config\certificates\"
+        ${EndIf}
     ${EndIf}
 
+
+
+
+
     # Install the launcher scripts
     createDirectory "$INSTDIR\licenses"
     SetOutPath "$INSTDIR"
@@ -419,6 +448,12 @@ SectionEnd
 !insertmacro MUI_PAGE_FINISH
 
 Function LaunchLink
-  #ExecShell "" "$SMPROGRAMS\${APPNAME}\${APPNAME}.lnk"
-  Exec "$INSTDIR\i2pbrowser.bat"
+  ${If} ${Silent}
+    ReadEnvStr $0 RESTART_I2P
+    ${If} $0 != ""
+      Exec "$INSTDIR\i2pbrowser.bat"
+    ${EndIf}  
+  ${Else}
+    Exec "$INSTDIR\i2pbrowser.bat"
+  ${EndIf}
 FunctionEnd
diff --git a/src/nsis/i2pbrowser-jpackage.nsi b/src/nsis/i2pbrowser-jpackage.nsi
index e69de29..c5c464a 100644
--- a/src/nsis/i2pbrowser-jpackage.nsi
+++ b/src/nsis/i2pbrowser-jpackage.nsi
@@ -0,0 +1 @@
+!define I2P_VERSION 0.9.50
\ No newline at end of file