diff --git a/plugins/settings-sync/git/src/com/intellij/settingsSync/git/record/ChangeRecord.kt b/plugins/settings-sync/git/src/com/intellij/settingsSync/git/record/ChangeRecord.kt
index f58a606e14c8..38c048ef83d7 100644
--- a/plugins/settings-sync/git/src/com/intellij/settingsSync/git/record/ChangeRecord.kt
+++ b/plugins/settings-sync/git/src/com/intellij/settingsSync/git/record/ChangeRecord.kt
@@ -129,7 +129,7 @@ internal class ChangeRecord(commitId: Int,
       if (fileName == GitSettingsLog.PLUGINS_FILE) return SettingsCategory.PLUGINS
 
       //workaround empty category
-      return getCategory(fileName) ?: SettingsCategory.OTHER
+      return getCategory(fileName)?.first ?: SettingsCategory.OTHER
     }
 
     val changesCategories = changes.map { getChangeCategory(it) }.distinct().sortedBy { getCategoryOrder(it) }.map { toString(it) }
diff --git a/plugins/settings-sync/src/com/intellij/settingsSync/SettingsSyncBridge.kt b/plugins/settings-sync/src/com/intellij/settingsSync/SettingsSyncBridge.kt
index a154d149d59d..a14eec4e7f80 100644
--- a/plugins/settings-sync/src/com/intellij/settingsSync/SettingsSyncBridge.kt
+++ b/plugins/settings-sync/src/com/intellij/settingsSync/SettingsSyncBridge.kt
@@ -92,6 +92,9 @@ class SettingsSyncBridge(
     coroutineScope.launch {
       withProgressText(SettingsSyncBundle.message(initMode.messageKey)) {
         try {
+          // Always explicitly flush settings – if this is not done before sending sync events, then remotely synced settings
+          // might not contain the most up–to–date settings state (e.g. sync settings will be stale).
+          saveIdeSettings()
           settingsLog.initialize()
 
           // the queue is not activated initially => events will be collected but not processed until we perform all initialization tasks
diff --git a/plugins/settings-sync/src/com/intellij/settingsSync/SettingsSyncFiltering.kt b/plugins/settings-sync/src/com/intellij/settingsSync/SettingsSyncFiltering.kt
index fa83bc6a90fc..82c7606cac9b 100644
--- a/plugins/settings-sync/src/com/intellij/settingsSync/SettingsSyncFiltering.kt
+++ b/plugins/settings-sync/src/com/intellij/settingsSync/SettingsSyncFiltering.kt
@@ -10,20 +10,19 @@ import com.intellij.openapi.util.text.StringUtil
 import com.intellij.serviceContainer.ComponentManagerImpl
 import com.intellij.settingsSync.config.EDITOR_FONT_SUBCATEGORY_ID
 import java.util.concurrent.ConcurrentHashMap
-import java.util.concurrent.ConcurrentMap
 
 internal fun isSyncCategoryEnabled(fileSpec: String): Boolean {
   val rawFileSpec = removeOsPrefix(fileSpec)
   if (rawFileSpec == SettingsSyncSettings.FILE_SPEC)
     return true
 
-  val category = getSchemeCategory(rawFileSpec) ?: getCategory(rawFileSpec) ?: return false
+  val (category, subCategory) = getSchemeCategory(rawFileSpec) ?: getCategory(rawFileSpec) ?: return false
 
   if (category != SettingsCategory.OTHER && SettingsSyncSettings.getInstance().isCategoryEnabled(category)) {
-    val subCategory = getSubCategory(fileSpec)
     if (subCategory != null) {
       return SettingsSyncSettings.getInstance().isSubcategoryEnabled(category, subCategory)
     }
+
     return true
   }
   return false
@@ -34,26 +33,22 @@ private fun removeOsPrefix(fileSpec: String): String {
   return if (fileSpec.startsWith(osPrefix)) StringUtil.trimStart(fileSpec, osPrefix) else fileSpec
 }
 
-private fun getCategory(componentClasses: List<Class<PersistentStateComponent<Any>>>): SettingsCategory {
-  when {
-    componentClasses.isEmpty() -> return SettingsCategory.OTHER
-    componentClasses.size == 1 -> return ComponentCategorizer.getCategory(componentClasses[0])
-    else -> {
-      componentClasses.forEach {
-        val category = ComponentCategorizer.getCategory(it)
-        if (category != SettingsCategory.OTHER) {
-          // Once found, ignore any other possibly conflicting definitions
-          return category
-        }
-      }
-      return SettingsCategory.OTHER
+private fun getCategory(fileName: String, componentClasses: List<Class<PersistentStateComponent<Any>>>): Pair<SettingsCategory, String?> {
+  componentClasses.forEach {
+    val category = ComponentCategorizer.getCategory(it)
+
+    if (category != SettingsCategory.OTHER) {
+      // Once found, ignore any other possibly conflicting definitions
+      return (category to getSubCategory(fileName))
     }
   }
+
+  return SettingsCategory.OTHER to null
 }
 
-private val categoryCache: ConcurrentMap<String, SettingsCategory> = ConcurrentHashMap()
+private val categoryCache: ConcurrentHashMap<String, Pair<SettingsCategory, String?>> = ConcurrentHashMap()
 
-fun getCategory(fileName: String): SettingsCategory? {
+fun getCategory(fileName: String): Pair<SettingsCategory, String?>? {
   categoryCache[fileName]?.let { cachedCategory ->
     return cachedCategory
   }
@@ -64,14 +59,14 @@ fun getCategory(fileName: String): SettingsCategory? {
     return null
   }
 
-  val category = getSchemeCategory(fileName) ?: getCategory(componentClasses)
+  val category = getSchemeCategory(fileName) ?: getCategory(fileName, componentClasses)
 
   categoryCache[fileName] = category
 
   return category
 }
 
-private fun getSchemeCategory(fileSpec: String): SettingsCategory? {
+private fun getSchemeCategory(fileSpec: String): Pair<SettingsCategory, String?>? {
   // fileSpec is e.g. keymaps/mykeymap.xml
   val separatorIndex = fileSpec.indexOf("/")
   val directoryName = if (separatorIndex >= 0) fileSpec.substring(0, separatorIndex) else fileSpec  // e.g. 'keymaps'
@@ -82,12 +77,13 @@ private fun getSchemeCategory(fileSpec: String): SettingsCategory? {
       settingsCategory = it.getSettingsCategory()
     }
   }
-  return settingsCategory
+  if (settingsCategory == null) {
+    return null
+  }
+
+  return settingsCategory!! to null
 }
 
-fun getFileSpec(path: String): String {
-  return removeOsPrefix(path)
-}
 
 private fun getSubCategory(fileSpec: String): String? {
   if (fileSpec == AppEditorFontOptions.STORAGE_NAME)
diff --git a/plugins/settings-sync/src/com/intellij/settingsSync/config/SyncPluginsGroup.kt b/plugins/settings-sync/src/com/intellij/settingsSync/config/SyncPluginsGroup.kt
index d1f51c023cb8..ec71b05f4511 100644
--- a/plugins/settings-sync/src/com/intellij/settingsSync/config/SyncPluginsGroup.kt
+++ b/plugins/settings-sync/src/com/intellij/settingsSync/config/SyncPluginsGroup.kt
@@ -18,6 +18,7 @@ internal class SyncPluginsGroup : SyncSubcategoryGroup {
     PluginManagerCore.plugins.forEach {
       if (!it.isBundled && SettingsSyncPluginCategoryFinder.getPluginCategory(it) == SettingsCategory.PLUGINS) {
         bundledPluginsDescriptor.isSubGroupEnd = true
+        // NOTE: the code in `com.intellij.settingsSync.SettingsSyncFilteringKt.getSubCategory` relies on the value being plugin ID
         descriptors.add(getOrCreateDescriptor(it.name, it.pluginId.idString))
       }
     }