diff --git a/share/translations/keepassxc_en.ts b/share/translations/keepassxc_en.ts
index d30b2e772..b9e442b80 100644
--- a/share/translations/keepassxc_en.ts
+++ b/share/translations/keepassxc_en.ts
@@ -3533,6 +3533,15 @@ Do you want to save the changes to your database?</source>
 Error: %1</source>
         <translation type="unfinished"></translation>
     </message>
+    <message>
+        <source>Confirm Overwrite Attachment</source>
+        <translation type="unfinished"></translation>
+    </message>
+    <message>
+        <source>Attachment &quot;%1&quot; already exists. 
+Would you like to overwrite the existing attachment?</source>
+        <translation type="unfinished"></translation>
+    </message>
 </context>
 <context>
     <name>EntryAttributesModel</name>
diff --git a/src/gui/entry/EntryAttachmentsWidget.cpp b/src/gui/entry/EntryAttachmentsWidget.cpp
index aeed9f4d2..33c97df96 100644
--- a/src/gui/entry/EntryAttachmentsWidget.cpp
+++ b/src/gui/entry/EntryAttachmentsWidget.cpp
@@ -152,7 +152,7 @@ void EntryAttachmentsWidget::insertAttachments()
     if (filenames.isEmpty()) {
         return;
     }
-    const auto confirmedFileNames = confirmLargeAttachments(filenames);
+    const auto confirmedFileNames = confirmAttachmentSelection(filenames);
     if (confirmedFileNames.isEmpty()) {
         return;
     }
@@ -342,28 +342,44 @@ bool EntryAttachmentsWidget::insertAttachments(const QStringList& filenames, QSt
     return errors.isEmpty();
 }
 
-QStringList EntryAttachmentsWidget::confirmLargeAttachments(const QStringList& filenames)
+QStringList EntryAttachmentsWidget::confirmAttachmentSelection(const QStringList& filenames)
 {
-    const QString confirmation(tr("%1 is a big file (%2 MB).\nYour database may get very large and reduce "
-                                  "performance.\n\nAre you sure to add this file?"));
     QStringList confirmedFileNames;
     for (const auto& file : filenames) {
-        QFileInfo fileInfo(file);
-        double size = fileInfo.size() / (1024.0 * 1024.0);
-        // Ask for confirmation before adding files over 5 MB in size
-        if (size > 5.0) {
-            auto fileName = fileInfo.fileName();
+        const QFileInfo fileInfo(file);
+        auto fileName = fileInfo.fileName();
+
+        // Ask for confirmation if overwriting an existing attachment
+        if (m_entryAttachments->hasKey(fileName)) {
             auto result = MessageBox::question(this,
-                                               tr("Confirm Attachment"),
-                                               confirmation.arg(fileName, QString::number(size, 'f', 1)),
-                                               MessageBox::Yes | MessageBox::No,
+                                               tr("Confirm Overwrite Attachment"),
+                                               tr("Attachment \"%1\" already exists. \n"
+                                                  "Would you like to overwrite the existing attachment?")
+                                                   .arg(fileName),
+                                               MessageBox::Overwrite | MessageBox::No,
                                                MessageBox::No);
-            if (result == MessageBox::Yes) {
-                confirmedFileNames << file;
+            if (result == MessageBox::No) {
+                continue;
             }
-        } else {
-            confirmedFileNames << file;
         }
+
+        // Ask for confirmation before adding files over 5 MB in size
+        double size = fileInfo.size() / (1024.0 * 1024.0);
+        if (size > 5.0) {
+            auto result =
+                MessageBox::question(this,
+                                     tr("Confirm Attachment"),
+                                     tr("%1 is a big file (%2 MB).\nYour database may get very large and reduce "
+                                        "performance.\n\nAre you sure to add this file?")
+                                         .arg(fileName, QString::number(size, 'f', 1)),
+                                     MessageBox::Yes | MessageBox::No,
+                                     MessageBox::No);
+            if (result == MessageBox::No) {
+                continue;
+            }
+        }
+
+        confirmedFileNames << file;
     }
 
     return confirmedFileNames;
diff --git a/src/gui/entry/EntryAttachmentsWidget.h b/src/gui/entry/EntryAttachmentsWidget.h
index 53d5076e2..9d64ed31b 100644
--- a/src/gui/entry/EntryAttachmentsWidget.h
+++ b/src/gui/entry/EntryAttachmentsWidget.h
@@ -69,7 +69,7 @@ private slots:
 private:
     bool insertAttachments(const QStringList& fileNames, QString& errorMessage);
 
-    QStringList confirmLargeAttachments(const QStringList& filenames);
+    QStringList confirmAttachmentSelection(const QStringList& filenames);
 
     bool eventFilter(QObject* watched, QEvent* event) override;