diff --git a/src/core/AutoTypeAssociations.cpp b/src/core/AutoTypeAssociations.cpp
index 5ec4eb3b..3d7a2c36 100644
--- a/src/core/AutoTypeAssociations.cpp
+++ b/src/core/AutoTypeAssociations.cpp
@@ -103,6 +103,15 @@ int AutoTypeAssociations::size() const
     return m_associations.size();
 }
 
+int AutoTypeAssociations::associationsSize() const
+{
+    int size = 0;
+    foreach (const Association &association, m_associations) {
+        size += association.sequence.toUtf8().size() + association.window.toUtf8().size();
+    }
+    return size;
+}
+
 void AutoTypeAssociations::clear()
 {
     m_associations.clear();
diff --git a/src/core/AutoTypeAssociations.h b/src/core/AutoTypeAssociations.h
index 61ef3fd4..31e58cda 100644
--- a/src/core/AutoTypeAssociations.h
+++ b/src/core/AutoTypeAssociations.h
@@ -43,6 +43,7 @@ public:
     AutoTypeAssociations::Association get(int index) const;
     QList<AutoTypeAssociations::Association> getAll() const;
     int size() const;
+    int associationsSize() const;
     void clear();
 
 private:
diff --git a/src/core/Entry.cpp b/src/core/Entry.cpp
index ed886083..b8e58929 100644
--- a/src/core/Entry.cpp
+++ b/src/core/Entry.cpp
@@ -582,7 +582,7 @@ void Entry::truncateHistory()
     int histMaxSize = db->metadata()->historyMaxSize();
     if (histMaxSize > -1) {
         int size = 0;
-        QSet<QByteArray> foundAttachments = attachments()->values().toSet();
+        QSet<QByteArray> foundAttachments = attachments()->values();
 
         QMutableListIterator<Entry*> i(m_history);
         i.toBack();
@@ -592,12 +592,12 @@ void Entry::truncateHistory()
             // don't calculate size if it's already above the maximum
             if (size <= histMaxSize) {
                 size += historyItem->attributes()->attributesSize();
-
-                const QSet<QByteArray> newAttachments = historyItem->attachments()->values().toSet() - foundAttachments;
-                for (const QByteArray& attachment : newAttachments) {
-                    size += attachment.size();
+                size += historyItem->autoTypeAssociations()->associationsSize();
+                size += historyItem->attachments()->attachmentsSize(foundAttachments);
+                foreach( const QString &tag, historyItem->tags().split(QRegExp(",|;|:"), QString::SkipEmptyParts)){
+                    size += tag.toUtf8().size();
                 }
-                foundAttachments += newAttachments;
+                foundAttachments += historyItem->attachments()->values();
             }
 
             if (size > histMaxSize) {
diff --git a/src/core/EntryAttachments.cpp b/src/core/EntryAttachments.cpp
index 95755860..6d3e38bb 100644
--- a/src/core/EntryAttachments.cpp
+++ b/src/core/EntryAttachments.cpp
@@ -18,6 +18,7 @@
 #include "EntryAttachments.h"
 
 #include <QStringList>
+#include <QSet>
 
 EntryAttachments::EntryAttachments(QObject* parent)
     : QObject(parent)
@@ -34,9 +35,9 @@ bool EntryAttachments::hasKey(const QString& key) const
     return m_attachments.contains(key);
 }
 
-QList<QByteArray> EntryAttachments::values() const
+QSet<QByteArray> EntryAttachments::values() const
 {
-    return m_attachments.values();
+    return m_attachments.values().toSet();
 }
 
 QByteArray EntryAttachments::value(const QString& key) const
@@ -151,3 +152,13 @@ bool EntryAttachments::operator!=(const EntryAttachments& other) const
 {
     return m_attachments != other.m_attachments;
 }
+
+int EntryAttachments::attachmentsSize(const QSet<QByteArray> &ignoredAttachments) const
+{
+    int size = 0;
+    const QSet<QByteArray> consideredAttachments = m_attachments.values().toSet() - ignoredAttachments;
+    for (const QByteArray& attachment : consideredAttachments) {
+        size += attachment.size();
+    }
+    return size;
+}
diff --git a/src/core/EntryAttachments.h b/src/core/EntryAttachments.h
index 0dba9543..835a13dc 100644
--- a/src/core/EntryAttachments.h
+++ b/src/core/EntryAttachments.h
@@ -31,7 +31,7 @@ public:
     explicit EntryAttachments(QObject* parent = nullptr);
     QList<QString> keys() const;
     bool hasKey(const QString& key) const;
-    QList<QByteArray> values() const;
+    QSet<QByteArray> values() const;
     QByteArray value(const QString& key) const;
     void set(const QString& key, const QByteArray& value);
     void remove(const QString& key);
@@ -41,6 +41,7 @@ public:
     void copyDataFrom(const EntryAttachments* other);
     bool operator==(const EntryAttachments& other) const;
     bool operator!=(const EntryAttachments& other) const;
+    int attachmentsSize(const QSet<QByteArray> &ignoredAttachments) const;
 
 signals:
     void modified();
diff --git a/src/core/EntryAttributes.cpp b/src/core/EntryAttributes.cpp
index 8cc7f2f0..4297f10a 100644
--- a/src/core/EntryAttributes.cpp
+++ b/src/core/EntryAttributes.cpp
@@ -283,14 +283,14 @@ void EntryAttributes::clear()
     emit modified();
 }
 
-int EntryAttributes::attributesSize()
+int EntryAttributes::attributesSize() const
 {
     int size = 0;
 
     QMapIterator<QString, QString> i(m_attributes);
     while (i.hasNext()) {
         i.next();
-        size += i.value().toUtf8().size();
+        size += i.key().toUtf8().size() + i.value().toUtf8().size();
     }
     return size;
 }
diff --git a/src/core/EntryAttributes.h b/src/core/EntryAttributes.h
index f483b8a9..3eca9171 100644
--- a/src/core/EntryAttributes.h
+++ b/src/core/EntryAttributes.h
@@ -45,7 +45,7 @@ public:
     void copyCustomKeysFrom(const EntryAttributes* other);
     bool areCustomKeysDifferent(const EntryAttributes* other);
     void clear();
-    int attributesSize();
+    int attributesSize() const;
     void copyDataFrom(const EntryAttributes* other);
     bool operator==(const EntryAttributes& other) const;
     bool operator!=(const EntryAttributes& other) const;