diff --git a/app/src/main/java/com/kunzisoft/keepass/activities/EntryEditActivity.kt b/app/src/main/java/com/kunzisoft/keepass/activities/EntryEditActivity.kt
index d293edb5a..dd7cc9b7a 100644
--- a/app/src/main/java/com/kunzisoft/keepass/activities/EntryEditActivity.kt
+++ b/app/src/main/java/com/kunzisoft/keepass/activities/EntryEditActivity.kt
@@ -41,10 +41,7 @@ import com.kunzisoft.keepass.activities.dialogs.*
 import com.kunzisoft.keepass.activities.dialogs.FileTooBigDialogFragment.Companion.MAX_WARNING_BINARY_FILE
 import com.kunzisoft.keepass.activities.helpers.SelectFileHelper
 import com.kunzisoft.keepass.activities.lock.LockingActivity
-import com.kunzisoft.keepass.database.element.Database
-import com.kunzisoft.keepass.database.element.DateInstant
-import com.kunzisoft.keepass.database.element.Entry
-import com.kunzisoft.keepass.database.element.Group
+import com.kunzisoft.keepass.database.element.*
 import com.kunzisoft.keepass.database.element.icon.IconImage
 import com.kunzisoft.keepass.database.element.icon.IconImageStandard
 import com.kunzisoft.keepass.database.element.node.NodeId
@@ -76,7 +73,8 @@ class EntryEditActivity : LockingActivity(),
         SetOTPDialogFragment.CreateOtpListener,
         DatePickerDialog.OnDateSetListener,
         TimePickerDialog.OnTimeSetListener,
-        FileTooBigDialogFragment.ActionChooseListener {
+        FileTooBigDialogFragment.ActionChooseListener,
+        ReplaceFileDialogFragment.ActionChooseListener {
 
     private var mDatabase: Database? = null
 
@@ -437,9 +435,22 @@ class EntryEditActivity : LockingActivity(),
         }
     }
 
+    override fun onValidateReplaceFile(attachmentToUploadUri: Uri?, entryAttachment: EntryAttachment?) {
+        if (attachmentToUploadUri != null && entryAttachment != null) {
+            mAttachmentFileBinderManager?.startUploadAttachment(attachmentToUploadUri, entryAttachment)
+        }
+    }
+
     private fun buildNewAttachment(attachmentToUploadUri: Uri, fileName: String) {
         mDatabase?.buildNewAttachment(applicationContext.filesDir, fileName)?.let { entryAttachment ->
-            mAttachmentFileBinderManager?.startUploadAttachment(attachmentToUploadUri, entryAttachment)
+            // Ask to replace the current attachment
+            if ((mDatabase?.allowMultipleAttachments != true && entryEditContentsView?.containsAttachment() == true) ||
+                    entryEditContentsView?.containsAttachment(EntryAttachmentState(entryAttachment, StreamDirection.UPLOAD)) == true) {
+                ReplaceFileDialogFragment.build(attachmentToUploadUri, entryAttachment)
+                        .show(supportFragmentManager, "replacementFileFragment")
+            } else {
+                mAttachmentFileBinderManager?.startUploadAttachment(attachmentToUploadUri, entryAttachment)
+            }
         }
     }
 
diff --git a/app/src/main/java/com/kunzisoft/keepass/activities/dialogs/ReplaceAttachmentDialogFragment.kt b/app/src/main/java/com/kunzisoft/keepass/activities/dialogs/ReplaceAttachmentDialogFragment.kt
new file mode 100644
index 000000000..06d039a04
--- /dev/null
+++ b/app/src/main/java/com/kunzisoft/keepass/activities/dialogs/ReplaceAttachmentDialogFragment.kt
@@ -0,0 +1,91 @@
+/*
+ * Copyright 2019 Jeremy Jamet / Kunzisoft.
+ *
+ * This file is part of KeePassDX.
+ *
+ *  KeePassDX is free software: you can redistribute it and/or modify
+ *  it under the terms of the GNU General Public License as published by
+ *  the Free Software Foundation, either version 3 of the License, or
+ *  (at your option) any later version.
+ *
+ *  KeePassDX is distributed in the hope that it will be useful,
+ *  but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *  MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ *  GNU General Public License for more details.
+ *
+ *  You should have received a copy of the GNU General Public License
+ *  along with KeePassDX.  If not, see <http://www.gnu.org/licenses/>.
+ *
+ */
+package com.kunzisoft.keepass.activities.dialogs
+
+import android.app.Dialog
+import android.content.Context
+import android.net.Uri
+import android.os.Bundle
+import android.text.SpannableStringBuilder
+import androidx.appcompat.app.AlertDialog
+import androidx.fragment.app.DialogFragment
+import com.kunzisoft.keepass.R
+import com.kunzisoft.keepass.database.element.EntryAttachment
+
+/**
+ * Custom Dialog to confirm big file to upload
+ */
+class ReplaceFileDialogFragment : DialogFragment() {
+
+    private var mActionChooseListener: ActionChooseListener? = null
+
+    override fun onAttach(context: Context) {
+        super.onAttach(context)
+        // Verify that the host activity implements the callback interface
+        try {
+            mActionChooseListener = context as ActionChooseListener
+        } catch (e: ClassCastException) {
+            throw ClassCastException(context.toString()
+                    + " must implement " + ActionChooseListener::class.java.name)
+        }
+    }
+
+    override fun onCreateDialog(savedInstanceState: Bundle?): Dialog {
+        activity?.let { activity ->
+            // Use the Builder class for convenient dialog construction
+            val builder = AlertDialog.Builder(activity)
+            builder.setMessage(SpannableStringBuilder().apply {
+                append(getString(R.string.warning_replace_file))
+                append("\n\n")
+                append(getString(R.string.warning_sure_add_file))
+            })
+            builder.setPositiveButton(android.R.string.yes) { _, _ ->
+                mActionChooseListener?.onValidateReplaceFile(
+                        arguments?.getParcelable(KEY_FILE_URI),
+                        arguments?.getParcelable(KEY_ENTRY_ATTACHMENT))
+            }
+            builder.setNegativeButton(android.R.string.no) { _, _ ->
+                dismiss()
+            }
+            // Create the AlertDialog object and return it
+            return builder.create()
+        }
+        return super.onCreateDialog(savedInstanceState)
+    }
+
+    interface ActionChooseListener {
+        fun onValidateReplaceFile(attachmentToUploadUri: Uri?, entryAttachment: EntryAttachment?)
+    }
+
+    companion object {
+        private const val KEY_FILE_URI = "KEY_FILE_URI"
+        private const val KEY_ENTRY_ATTACHMENT = "KEY_ENTRY_ATTACHMENT"
+
+        fun build(attachmentToUploadUri: Uri,
+                  entryAttachment: EntryAttachment): ReplaceFileDialogFragment {
+            val fragment = ReplaceFileDialogFragment()
+            fragment.arguments = Bundle().apply {
+                putParcelable(KEY_FILE_URI, attachmentToUploadUri)
+                putParcelable(KEY_ENTRY_ATTACHMENT, entryAttachment)
+            }
+            return fragment
+        }
+    }
+}
diff --git a/app/src/main/java/com/kunzisoft/keepass/adapters/AnimatedItemsAdapter.kt b/app/src/main/java/com/kunzisoft/keepass/adapters/AnimatedItemsAdapter.kt
index a4deb31eb..d1fa9edc8 100644
--- a/app/src/main/java/com/kunzisoft/keepass/adapters/AnimatedItemsAdapter.kt
+++ b/app/src/main/java/com/kunzisoft/keepass/adapters/AnimatedItemsAdapter.kt
@@ -32,6 +32,14 @@ abstract class AnimatedItemsAdapter<Item, T: RecyclerView.ViewHolder>(val contex
         onListSizeChangedListener?.invoke(previousSize, itemsList.size)
     }
 
+    open fun isEmpty(): Boolean {
+        return itemsList.isEmpty()
+    }
+
+    open fun contains(item: Item): Boolean {
+        return itemsList.contains(item)
+    }
+
     open fun putItem(item: Item) {
         val previousSize = itemsList.size
         if (itemsList.contains(item)) {
diff --git a/app/src/main/java/com/kunzisoft/keepass/view/EntryEditContentsView.kt b/app/src/main/java/com/kunzisoft/keepass/view/EntryEditContentsView.kt
index ef585d882..1827e14af 100644
--- a/app/src/main/java/com/kunzisoft/keepass/view/EntryEditContentsView.kt
+++ b/app/src/main/java/com/kunzisoft/keepass/view/EntryEditContentsView.kt
@@ -294,6 +294,14 @@ class EntryEditContentsView @JvmOverloads constructor(context: Context,
         }
     }
 
+    fun containsAttachment(): Boolean {
+        return !attachmentsAdapter.isEmpty()
+    }
+
+    fun containsAttachment(attachment: EntryAttachmentState): Boolean {
+        return attachmentsAdapter.contains(attachment)
+    }
+
     fun putAttachment(attachment: EntryAttachmentState) {
         attachmentsContainerView.visibility = View.VISIBLE
         attachmentsAdapter.putItem(attachment)
diff --git a/app/src/main/res/values/strings.xml b/app/src/main/res/values/strings.xml
index 02be54d4a..61a30a133 100644
--- a/app/src/main/res/values/strings.xml
+++ b/app/src/main/res/values/strings.xml
@@ -258,6 +258,7 @@
     <string name="warning_no_encryption_key">Continue without encryption key?</string>
     <string name="warning_permanently_delete_nodes">Permanently delete selected nodes?</string>
     <string name="warning_file_too_big">A KeePass database is supposed to contain only small utility files (such as PGP key files).\n\nYour database may get very large and reduce performance with this upload.</string>
+    <string name="warning_replace_file">Uploading this file will replace the existing one.</string>
     <string name="warning_sure_add_file">Add the file anyway?</string>
     <string name="version_label">Version %1$s</string>
     <string name="build_label">Build %1$s</string>