diff --git a/src/com/fsck/k9/preferences/Settings.java b/src/com/fsck/k9/preferences/Settings.java
index 7cc1e701c..305224f83 100644
--- a/src/com/fsck/k9/preferences/Settings.java
+++ b/src/com/fsck/k9/preferences/Settings.java
@@ -5,6 +5,7 @@ import java.util.HashMap;
 import java.util.HashSet;
 import java.util.Map;
 import java.util.Set;
+import java.util.SortedMap;
 import java.util.TreeMap;
 import java.util.Map.Entry;
 
@@ -44,15 +45,25 @@ public class Settings {
         for (Map.Entry<String, TreeMap<Integer, SettingsDescription>> versionedSetting :
                 settings.entrySet()) {
 
-            Entry<Integer, SettingsDescription> setting =
-                versionedSetting.getValue().floorEntry(version);
+            // Get the setting description with the highest version lower than or equal to the
+            // supplied content version.
+            TreeMap<Integer, SettingsDescription> versions = versionedSetting.getValue();
+            SortedMap<Integer, SettingsDescription> headMap = versions.headMap(version + 1);
 
-            if (setting == null) {
+            // Skip this setting if it was introduced after 'version'
+            if (headMap.size() == 0) {
+                continue;
+            }
+
+            Integer settingVersion = headMap.lastKey();
+            SettingsDescription desc = versions.get(settingVersion);
+
+            // Skip this setting if it is no longer used in 'version'
+            if (desc == null) {
                 continue;
             }
 
             String key = versionedSetting.getKey();
-            SettingsDescription desc = setting.getValue();
 
             boolean useDefaultValue;
             if (!importedSettings.containsKey(key)) {
@@ -127,7 +138,7 @@ public class Settings {
                     // Check if it was already added to upgradedSettings by the SettingsUpgrader
                     if (!upgradedSettings.containsKey(settingName)) {
                         // Insert default value to upgradedSettings
-                        SettingsDescription setting = versionedSettings.firstEntry().getValue();
+                        SettingsDescription setting = versionedSettings.get(toVersion);
                         Object defaultValue = setting.getDefaultValue();
                         upgradedSettings.put(settingName, defaultValue);
 
@@ -140,8 +151,9 @@ public class Settings {
                 }
 
                 // Handle removed settings
-                Entry<Integer, SettingsDescription> lastEntry = versionedSettings.lastEntry();
-                if (lastEntry.getKey().intValue() == toVersion && lastEntry.getValue() == null) {
+                Integer highestVersion = versionedSettings.lastKey();
+                if (highestVersion.intValue() == toVersion &&
+                        versionedSettings.get(highestVersion) == null) {
                     upgradedSettings.remove(settingName);
                     if (deletedSettings == null) {
                         deletedSettings = new HashSet<String>();
@@ -179,8 +191,10 @@ public class Settings {
             String settingName = setting.getKey();
             Object internalValue = setting.getValue();
 
-            SettingsDescription settingDesc =
-                settingDescriptions.get(settingName).lastEntry().getValue();
+            TreeMap<Integer, SettingsDescription> versionedSetting =
+                settingDescriptions.get(settingName);
+            Integer highestVersion = versionedSetting.lastKey();
+            SettingsDescription settingDesc = versionedSetting.get(highestVersion);
 
             if (settingDesc != null) {
                 String stringValue = settingDesc.toString(internalValue);
diff --git a/src/com/fsck/k9/preferences/SettingsExporter.java b/src/com/fsck/k9/preferences/SettingsExporter.java
index cb0ea4431..2497376aa 100644
--- a/src/com/fsck/k9/preferences/SettingsExporter.java
+++ b/src/com/fsck/k9/preferences/SettingsExporter.java
@@ -172,7 +172,9 @@ public class SettingsExporter {
 
             String key = versionedSetting.getKey();
             String valueString = (String) prefs.get(key);
-            SettingsDescription setting = versionedSetting.getValue().lastEntry().getValue();
+            TreeMap<Integer, SettingsDescription> versions = versionedSetting.getValue();
+            Integer highestVersion = versions.lastKey();
+            SettingsDescription setting = versions.get(highestVersion);
             if (setting == null) {
                 // Setting was removed.
                 continue;
@@ -322,7 +324,8 @@ public class SettingsExporter {
                 AccountSettings.SETTINGS.get(keyPart);
 
             if (versionedSetting != null) {
-                SettingsDescription setting = versionedSetting.lastEntry().getValue();
+                Integer highestVersion = versionedSetting.lastKey();
+                SettingsDescription setting = versionedSetting.get(highestVersion);
 
                 if (setting != null) {
                     // Only export account settings that can be found in AccountSettings.SETTINGS
@@ -416,7 +419,8 @@ public class SettingsExporter {
                 IdentitySettings.SETTINGS.get(identityKey);
 
             if (versionedSetting != null) {
-                SettingsDescription setting = versionedSetting.lastEntry().getValue();
+                Integer highestVersion = versionedSetting.lastKey();
+                SettingsDescription setting = versionedSetting.get(highestVersion);
 
                 if (setting != null) {
                     // Only write settings that have an entry in IdentitySettings.SETTINGS
@@ -467,7 +471,8 @@ public class SettingsExporter {
                 FolderSettings.SETTINGS.get(folderKey);
 
             if (versionedSetting != null) {
-                SettingsDescription setting = versionedSetting.lastEntry().getValue();
+                Integer highestVersion = versionedSetting.lastKey();
+                SettingsDescription setting = versionedSetting.get(highestVersion);
 
                 if (setting != null) {
                     // Only write settings that have an entry in FolderSettings.SETTINGS