diff --git a/.github/workflows/win-exe.yml b/.github/workflows/win-exe.yml
index df67c1dcb..8a66e524b 100644
--- a/.github/workflows/win-exe.yml
+++ b/.github/workflows/win-exe.yml
@@ -112,17 +112,17 @@ jobs:
           --java-options "-Xmx256m"
           --java-options "-Dcryptomator.appVersion=\"${{ needs.get-version.outputs.semVerStr }}\""
           --java-options "-Dfile.encoding=\"utf-8\""
-          --java-options "-Dcryptomator.logDir=\"~/AppData/Roaming/Cryptomator\""
-          --java-options "-Dcryptomator.pluginDir=\"~/AppData/Roaming/Cryptomator/Plugins\""
-          --java-options "-Dcryptomator.settingsPath=\"~/AppData/Roaming/Cryptomator/settings.json\""
-          --java-options "-Dcryptomator.p12Path=\"~/AppData/Roaming/Cryptomator/key.p12\""
-          --java-options "-Dcryptomator.ipcSocketPath=\"~/AppData/Roaming/Cryptomator/ipc.socket\""
-          --java-options "-Dcryptomator.mountPointsDir=\"~/Cryptomator\""
+          --java-options "-Dcryptomator.logDir=\"@{localappdata}/Cryptomator\""
+          --java-options "-Dcryptomator.pluginDir=\"@{appdata}/Cryptomator/Plugins\""
+          --java-options "-Dcryptomator.settingsPath=\"@{appdata}/Cryptomator/settings.json;@{userhome}/AppData/Roaming/Cryptomator/settings.json\""
+          --java-options "-Dcryptomator.p12Path=\"@{appdata}/Cryptomator/key.p12;@{userhome}/AppData/Roaming/Cryptomator/key.p12\""
+          --java-options "-Dcryptomator.ipcSocketPath=\"@{localappdata}/Cryptomator/ipc.socket\""
+          --java-options "-Dcryptomator.mountPointsDir=\"@{userhome}/Cryptomator\""
           --java-options "-Dcryptomator.loopbackAlias=\"${{ env.LOOPBACK_ALIAS }}\""
           --java-options "-Dcryptomator.showTrayIcon=true"
           --java-options "-Dcryptomator.buildNumber=\"msi-${{ needs.get-version.outputs.revNum }}\""
           --java-options "-Dcryptomator.integrationsWin.autoStartShellLinkName=\"Cryptomator\""
-          --java-options "-Dcryptomator.integrationsWin.keychainPaths=\"~/AppData/Roaming/Cryptomator/keychain.json\""
+          --java-options "-Dcryptomator.integrationsWin.keychainPaths=\"@{appdata}/Cryptomator/keychain.json;@{userhome}/AppData/Roaming/Cryptomator/keychain.json\""
           --java-options "-Djavafx.verbose=${{ inputs.isDebug }}"
           --resource-dir dist/win/resources
           --icon dist/win/resources/Cryptomator.ico
diff --git a/.idea/runConfigurations/Cryptomator_Windows.xml b/.idea/runConfigurations/Cryptomator_Windows.xml
index 3c4ecc4a3..b1f7c11b3 100644
--- a/.idea/runConfigurations/Cryptomator_Windows.xml
+++ b/.idea/runConfigurations/Cryptomator_Windows.xml
@@ -2,7 +2,7 @@
   <configuration default="false" name="Cryptomator Windows" type="Application" factoryName="Application">
     <option name="MAIN_CLASS_NAME" value="org.cryptomator.launcher.Cryptomator" />
     <module name="cryptomator" />
-    <option name="VM_PARAMETERS" value="-Dcryptomator.settingsPath=&quot;~/AppData/Roaming/Cryptomator/settings.json&quot; -Dcryptomator.ipcSocketPath=&quot;~/AppData/Roaming/Cryptomator/ipc.socket&quot; -Dcryptomator.logDir=&quot;~/AppData/Roaming/Cryptomator&quot; -Dcryptomator.pluginDir=&quot;~/AppData/Roaming/Cryptomator/Plugins&quot; -Dcryptomator.integrationsWin.keychainPaths=&quot;~/AppData/Roaming/Cryptomator/keychain.json&quot; -Dcryptomator.p12Path=&quot;~/AppData/Roaming/Cryptomator/key.p12&quot; -Dcryptomator.mountPointsDir=&quot;~/Cryptomator&quot; -Dcryptomator.showTrayIcon=true -Xss2m -Xmx512m --enable-preview --enable-native-access=org.cryptomator.jfuse.win" />
+    <option name="VM_PARAMETERS" value="-Dcryptomator.settingsPath=&quot;@{appdata}/Cryptomator/settings.json;@{userhome}/AppData/Roaming/Cryptomator/settings.json&quot; -Dcryptomator.ipcSocketPath=&quot;@{localappdata}/Cryptomator/ipc.socket&quot; -Dcryptomator.logDir=&quot;@{localappdata}/Cryptomator&quot; -Dcryptomator.pluginDir=&quot;@{appdata}/Cryptomator/Plugins&quot; -Dcryptomator.integrationsWin.keychainPaths=&quot;@{appdata}/Cryptomator/keychain.json;@{userhome}/AppData/Roaming/Cryptomator/keychain.json&quot; -Dcryptomator.p12Path=&quot;@{appdata}/Cryptomator/key.p12;@{userhome}/AppData/Roaming/Cryptomator/key.p12&quot; -Dcryptomator.mountPointsDir=&quot;@{userhome}/Cryptomator&quot; -Dcryptomator.showTrayIcon=true -Xss2m -Xmx512m --enable-preview --enable-native-access=org.cryptomator.jfuse.win" />
     <method v="2">
       <option name="Make" enabled="true" />
     </method>
diff --git a/.idea/runConfigurations/Cryptomator_Windows_Dev.xml b/.idea/runConfigurations/Cryptomator_Windows_Dev.xml
index 2093aee5e..425c774be 100644
--- a/.idea/runConfigurations/Cryptomator_Windows_Dev.xml
+++ b/.idea/runConfigurations/Cryptomator_Windows_Dev.xml
@@ -2,7 +2,7 @@
   <configuration default="false" name="Cryptomator Windows Dev" type="Application" factoryName="Application">
     <option name="MAIN_CLASS_NAME" value="org.cryptomator.launcher.Cryptomator" />
     <module name="cryptomator" />
-    <option name="VM_PARAMETERS" value="-Dcryptomator.settingsPath=&quot;~/AppData/Roaming/Cryptomator-Dev/settings.json&quot; -Dcryptomator.ipcSocketPath=&quot;~/AppData/Roaming/Cryptomator-Dev/ipc.socket&quot; -Dcryptomator.logDir=&quot;~/AppData/Roaming/Cryptomator-Dev&quot; -Dcryptomator.pluginDir=&quot;~/AppData/Roaming/Cryptomator-Dev/Plugins&quot; -Dcryptomator.integrationsWin.keychainPaths=&quot;~/AppData/Roaming/Cryptomator-Dev/keychain.json&quot; -Dcryptomator.p12Path=&quot;~/AppData/Roaming/Cryptomator-Dev/key.p12&quot; -Dcryptomator.mountPointsDir=&quot;~/Cryptomator-Dev&quot; -Dcryptomator.showTrayIcon=true -Xss2m -Xmx512m --enable-preview --enable-native-access=org.cryptomator.jfuse.win" />
+    <option name="VM_PARAMETERS" value="-Dcryptomator.settingsPath=&quot;@{appdata}/Cryptomator-Dev/settings.json;@{userhome}/AppData/Roaming/Cryptomator-Dev/settings.json&quot; -Dcryptomator.ipcSocketPath=&quot;@{localappdata}/Cryptomator-Dev/ipc.socket&quot; -Dcryptomator.logDir=&quot;@{localappdata}/Cryptomator-Dev&quot; -Dcryptomator.pluginDir=&quot;@{appdata}/Cryptomator-Dev/Plugins&quot; -Dcryptomator.integrationsWin.keychainPaths=&quot;@{appdata}/Cryptomator-Dev/keychain.json;@{userhome}/AppData/Roaming/Cryptomator-Dev/keychain.json&quot; -Dcryptomator.p12Path=&quot;@{appdata}/Cryptomator-Dev/key.p12;@{userhome}/AppData/Roaming/Cryptomator-Dev/key.p12&quot; -Dcryptomator.mountPointsDir=&quot;@{userhome}/Cryptomator-Dev&quot; -Dcryptomator.showTrayIcon=true -Xss2m -Xmx512m --enable-preview --enable-native-access=org.cryptomator.jfuse.win" />
     <method v="2">
       <option name="Make" enabled="true" />
     </method>
diff --git a/dist/win/build.ps1 b/dist/win/build.ps1
index 74532a96a..2e3d3b83d 100644
--- a/dist/win/build.ps1
+++ b/dist/win/build.ps1
@@ -82,15 +82,15 @@ if ($clean -and (Test-Path -Path $appPath)) {
 	--java-options "-Dcryptomator.appVersion=`"$semVerNo`"" `
 	--app-version "$semVerNo.$revisionNo" `
 	--java-options "-Dfile.encoding=`"utf-8`"" `
-	--java-options "-Dcryptomator.logDir=`"~/AppData/Roaming/$AppName`"" `
-	--java-options "-Dcryptomator.pluginDir=`"~/AppData/Roaming/$AppName/Plugins`"" `
-	--java-options "-Dcryptomator.settingsPath=`"~/AppData/Roaming/$AppName/settings.json`"" `
-	--java-options "-Dcryptomator.ipcSocketPath=`"~/AppData/Roaming/$AppName/ipc.socket`"" `
-	--java-options "-Dcryptomator.p12Path=`"~/AppData/Roaming/$AppName/key.p12`"" `
-	--java-options "-Dcryptomator.mountPointsDir=`"~/$AppName`"" `
+	--java-options "-Dcryptomator.logDir=`"@{localappdata}/$AppName`"" `
+	--java-options "-Dcryptomator.pluginDir=`"@{appdata}/$AppName/Plugins`"" `
+	--java-options "-Dcryptomator.settingsPath=`"@{appdata}/$AppName/settings.json;@{userhome}/AppData/Roaming/$AppName/settings.json`"" `
+	--java-options "-Dcryptomator.ipcSocketPath=`"@{localappdata}/$AppName/ipc.socket`"" `
+	--java-options "-Dcryptomator.p12Path=`"@{appdata}/$AppName/key.p12;@{userhome}/AppData/Roaming/$AppName/key.p12`"" `
+	--java-options "-Dcryptomator.mountPointsDir=`"@{userhome}/$AppName`"" `
 	--java-options "-Dcryptomator.loopbackAlias=`"$LoopbackAlias`"" `
 	--java-options "-Dcryptomator.integrationsWin.autoStartShellLinkName=`"$AppName`"" `
-	--java-options "-Dcryptomator.integrationsWin.keychainPaths=`"~/AppData/Roaming/$AppName/keychain.json`"" `
+	--java-options "-Dcryptomator.integrationsWin.keychainPaths=`"@{appdata}/$AppName/keychain.json;@{userhome}/AppData/Roaming/$AppName/keychain.json`"" `
 	--java-options "-Dcryptomator.showTrayIcon=true" `
 	--java-options "-Dcryptomator.buildNumber=`"msi-$revisionNo`"" `
 	--resource-dir resources `
diff --git a/src/main/java/org/cryptomator/common/Environment.java b/src/main/java/org/cryptomator/common/Environment.java
index f1cc6974d..d9dec7b89 100644
--- a/src/main/java/org/cryptomator/common/Environment.java
+++ b/src/main/java/org/cryptomator/common/Environment.java
@@ -2,6 +2,7 @@ package org.cryptomator.common;
 
 import com.google.common.base.Splitter;
 import com.google.common.base.Strings;
+import org.apache.commons.lang3.SystemUtils;
 import org.slf4j.Logger;
 import org.slf4j.LoggerFactory;
 
@@ -18,7 +19,7 @@ import java.util.stream.StreamSupport;
 public class Environment {
 
 	private static final Logger LOG = LoggerFactory.getLogger(Environment.class);
-	private static final char PATH_LIST_SEP = ':';
+	private static final char PATH_LIST_SEP = SystemUtils.IS_OS_WINDOWS? ';':':';
 	private static final int DEFAULT_MIN_PW_LENGTH = 8;
 	private static final String SETTINGS_PATH_PROP_NAME = "cryptomator.settingsPath";
 	private static final String IPC_SOCKET_PATH_PROP_NAME = "cryptomator.ipcSocketPath";
diff --git a/src/main/java/org/cryptomator/common/PropertiesPreprocessor.java b/src/main/java/org/cryptomator/common/PropertiesPreprocessor.java
index 785b249bf..683b04aa2 100644
--- a/src/main/java/org/cryptomator/common/PropertiesPreprocessor.java
+++ b/src/main/java/org/cryptomator/common/PropertiesPreprocessor.java
@@ -34,6 +34,7 @@ public class PropertiesPreprocessor {
 				switch (match.group(1)) {
 					case "appdir" -> ENV.get("APPDIR");
 					case "appdata" -> ENV.get("APPDATA");
+					case "localappdata" -> ENV.get("LOCALAPPDATA");
 					case "userhome" -> System.getProperty("user.home");
 					default -> {
 						LOG.warn("Found unknown variable @{{}} in property value {}.", match.group(), value);