diff --git a/src/core/Entry.cpp b/src/core/Entry.cpp
index a035f713..6cbf8211 100644
--- a/src/core/Entry.cpp
+++ b/src/core/Entry.cpp
@@ -337,17 +337,8 @@ void Entry::setExpiryTime(const QDateTime& dateTime)
     }
 }
 
-int Entry::getHistSize() {
-    int size = 0;
-
-    for(int i=0 ; i<m_history.size() ; i++) {
-        size += m_history[i]->getSize();
-    }
-    return size;
-}
-
-int Entry::getSize() {
-    return attributes()->attributesSize() + attachments()->attachmentsSize();
+int Entry::getSize(QList<QByteArray>* foundAttachements) {
+    return attributes()->attributesSize() + attachments()->attachmentsSize(foundAttachements);
 }
 
 QList<Entry*> Entry::historyItems()
@@ -366,18 +357,49 @@ void Entry::addHistoryItem(Entry* entry)
     Q_ASSERT(entry->uuid() == uuid());
 
     m_history.append(entry);
-    truncateHistory();
     Q_EMIT modified();
 }
 
 void Entry::truncateHistory() {
     const Database *db = database();
     if(db) {
-        while(m_history.size() > db->metadata()->historyMaxItems()) {
-            m_history.removeFirst();
+        int histMaxItems = db->metadata()->historyMaxItems();
+        if (histMaxItems > -1) {
+            int historyCount = 0;
+            QMutableListIterator<Entry*> i(m_history);
+            i.toBack();
+            while (i.hasPrevious()) {
+                historyCount++;
+                Entry* entry = i.previous();
+                if (historyCount > histMaxItems) {
+                    delete entry;
+                    i.remove();
+                }
+            }
         }
-        while(getHistSize() > db->metadata()->historyMaxSize()) {
-            m_history.removeFirst();
+
+        int histMaxSize = db->metadata()->historyMaxSize();
+        if (histMaxSize > -1) {
+            int size = 0;
+            QList<QByteArray>* foundAttachements = new QList<QByteArray>();
+            attachments()->attachmentsSize(foundAttachements);
+
+            QMutableListIterator<Entry*> i(m_history);
+            i.toBack();
+            while (i.hasPrevious()) {
+                Entry* entry = i.previous();
+                if (size > histMaxSize) {
+                    delete entry;
+                    i.remove();
+                }
+                else {
+                    size += entry->getSize(foundAttachements);
+                    if (size > histMaxSize) {
+                        delete entry;
+                        i.remove();
+                    }
+                }
+            }
         }
     }
 }
@@ -399,10 +421,10 @@ void Entry::beginUpdate()
 void Entry::endUpdate()
 {
     Q_ASSERT(m_tmpHistoryItem);
-
     if (m_modifiedSinceBegin) {
         m_tmpHistoryItem->setUpdateTimeinfo(true);
         addHistoryItem(m_tmpHistoryItem);
+        truncateHistory();
     }
     else {
         delete m_tmpHistoryItem;
diff --git a/src/core/Entry.h b/src/core/Entry.h
index 7bd32466..e51b7e95 100644
--- a/src/core/Entry.h
+++ b/src/core/Entry.h
@@ -108,8 +108,7 @@ public:
     void setNotes(const QString& notes);
     void setExpires(const bool& value);
     void setExpiryTime(const QDateTime& dateTime);
-    int getHistSize();
-    int getSize();
+    int getSize(QList<QByteArray>* foundAttachements);
 
     QList<Entry*> historyItems();
     const QList<Entry*>& historyItems() const;
diff --git a/src/core/EntryAttachments.cpp b/src/core/EntryAttachments.cpp
index 0e82c67e..0ce2d138 100644
--- a/src/core/EntryAttachments.cpp
+++ b/src/core/EntryAttachments.cpp
@@ -32,11 +32,6 @@ QByteArray EntryAttachments::value(const QString& key) const
     return m_attachments.value(key);
 }
 
-int EntryAttachments::dataSize(const QString& key)
-{
-    return m_attachments.value(key).size();
-}
-
 void EntryAttachments::set(const QString& key, const QByteArray& value)
 {
     bool emitModified = false;
@@ -92,11 +87,16 @@ void EntryAttachments::clear()
     Q_EMIT modified();
 }
 
-int EntryAttachments::attachmentsSize() {
+int EntryAttachments::attachmentsSize(QList<QByteArray>* foundAttachements) {
     int size = 0;
 
-    Q_FOREACH (const QString& key, keys()) {
-        size += dataSize(key);
+    QMapIterator<QString, QByteArray> i(m_attachments);
+    while (i.hasNext()) {
+        i.next();
+        if (!foundAttachements->contains(i.value())) {
+            foundAttachements->append(i.value());
+            size += i.value().size();
+        }
     }
     return size;
 }
diff --git a/src/core/EntryAttachments.h b/src/core/EntryAttachments.h
index 4ae32156..a4cfe304 100644
--- a/src/core/EntryAttachments.h
+++ b/src/core/EntryAttachments.h
@@ -29,11 +29,10 @@ public:
     explicit EntryAttachments(QObject* parent = 0);
     QList<QString> keys() const;
     QByteArray value(const QString& key) const;
-    int dataSize(const QString& key);
     void set(const QString& key, const QByteArray& value);
     void remove(const QString& key);
     void clear();
-    int attachmentsSize();
+    int attachmentsSize(QList<QByteArray> *foundAttachements);
     bool operator==(const EntryAttachments& other) const;
     bool operator!=(const EntryAttachments& other) const;
     EntryAttachments& operator=(EntryAttachments& other);
diff --git a/src/core/EntryAttributes.cpp b/src/core/EntryAttributes.cpp
index cccff9e8..66709b8e 100644
--- a/src/core/EntryAttributes.cpp
+++ b/src/core/EntryAttributes.cpp
@@ -36,11 +36,6 @@ QString EntryAttributes::value(const QString& key) const
     return m_attributes.value(key);
 }
 
-int EntryAttributes::valueSize(const QString& key)
-{
-    return m_attributes.value(key).size() * sizeof(QChar);
-}
-
 bool EntryAttributes::isProtected(const QString& key) const
 {
     return m_protectedAttributes.contains(key);
@@ -231,8 +226,10 @@ void EntryAttributes::clear()
 int EntryAttributes::attributesSize() {
     int size = 0;
 
-    Q_FOREACH (const QString& key, keys()) {
-        size += valueSize(key);
+    QMapIterator<QString, QString> i(m_attributes);
+    while (i.hasNext()) {
+        i.next();
+        size += i.value().toUtf8().size();
     }
     return size;
 }
diff --git a/src/core/EntryAttributes.h b/src/core/EntryAttributes.h
index c5f55d10..6f4dac8e 100644
--- a/src/core/EntryAttributes.h
+++ b/src/core/EntryAttributes.h
@@ -22,7 +22,6 @@
 #include <QtCore/QSet>
 #include <QtCore/QObject>
 #include <QtCore/QStringList>
-#include <QtCore/QChar>
 
 class EntryAttributes : public QObject
 {
@@ -32,7 +31,6 @@ public:
     explicit EntryAttributes(QObject* parent = 0);
     QList<QString> keys() const;
     QString value(const QString& key) const;
-    int valueSize(const QString& key);
     bool isProtected(const QString& key) const;
     void set(const QString& key, const QString& value, bool protect = false);
     void remove(const QString& key);
@@ -44,6 +42,7 @@ public:
     EntryAttributes& operator=(const EntryAttributes& other);
     bool operator==(const EntryAttributes& other) const;
     bool operator!=(const EntryAttributes& other) const;
+
     static const QStringList DEFAULT_ATTRIBUTES;
     static bool isDefaultAttribute(const QString& key);