diff --git a/client/components/admin/admin-general.vue b/client/components/admin/admin-general.vue
index 8804ee39..4f6989e9 100644
--- a/client/components/admin/admin-general.vue
+++ b/client/components/admin/admin-general.vue
@@ -177,6 +177,19 @@
                     persistent-hint
                     )
 
+              v-card.mt-5.animated.fadeInUp.wait-p6s
+                v-toolbar(color='primary', dark, dense, flat)
+                  v-toolbar-title.subtitle-1 File Handling
+                v-card-text
+                  v-switch.mt-0(
+                    inset
+                    label='Append timestamp to filenames'
+                    color='indigo'
+                    v-model='config.uploadAppendTimestampToFilename'
+                    persistent-hint
+                    hint='A timestamp will be appended to the end of the original filename to ensure each uploaded file will not overwrite others.'
+                    )
+
               v-card.mt-5.animated.fadeInUp.wait-p7s
                 v-toolbar(color='primary', dark, dense, flat)
                   v-toolbar-title.subtitle-1 {{$t('admin:general.editShortcuts')}}
@@ -293,7 +306,8 @@ export default {
         editMenuExternalBtn: false,
         editMenuExternalName: '',
         editMenuExternalIcon: '',
-        editMenuExternalUrl: ''
+        editMenuExternalUrl: '',
+        uploadAppendTimestampToFilename: false
       },
       metaRobots: [
         { text: 'Index', value: 'index' },
@@ -358,6 +372,7 @@ export default {
               $editMenuExternalName: String
               $editMenuExternalIcon: String
               $editMenuExternalUrl: String
+              $uploadAppendTimestampToFilename: Boolean
             ) {
               site {
                 updateConfig(
@@ -381,6 +396,7 @@ export default {
                   editMenuExternalName: $editMenuExternalName
                   editMenuExternalIcon: $editMenuExternalIcon
                   editMenuExternalUrl: $editMenuExternalUrl
+                  uploadAppendTimestampToFilename: $uploadAppendTimestampToFilename
                 ) {
                   responseResult {
                     succeeded
@@ -412,7 +428,8 @@ export default {
             editMenuExternalBtn: _.get(this.config, 'editMenuExternalBtn', false),
             editMenuExternalName: _.get(this.config, 'editMenuExternalName', ''),
             editMenuExternalIcon: _.get(this.config, 'editMenuExternalIcon', ''),
-            editMenuExternalUrl: _.get(this.config, 'editMenuExternalUrl', '')
+            editMenuExternalUrl: _.get(this.config, 'editMenuExternalUrl', ''),
+            uploadAppendTimestampToFilename: _.get(this.config, 'uploadAppendTimestampToFilename', false)
           },
           watchLoading (isLoading) {
             this.$store.commit(`loading${isLoading ? 'Start' : 'Stop'}`, 'admin-site-update')
@@ -473,6 +490,7 @@ export default {
               editMenuExternalName
               editMenuExternalIcon
               editMenuExternalUrl
+              uploadAppendTimestampToFilename
             }
           }
         }
diff --git a/server/app/data.yml b/server/app/data.yml
index a7fb78ae..4e5031a4 100644
--- a/server/app/data.yml
+++ b/server/app/data.yml
@@ -97,6 +97,7 @@ defaults:
       maxFiles: 10
       scanSVG: true
       forceDownload: true
+      appendTimestampToFilename: false
     flags:
       ldapdebug: false
       sqllog: false
diff --git a/server/controllers/upload.js b/server/controllers/upload.js
index 0b86c251..bfa453a6 100644
--- a/server/controllers/upload.js
+++ b/server/controllers/upload.js
@@ -78,9 +78,11 @@ router.post('/u', (req, res, next) => {
   // Sanitize filename
   fileMeta.originalname = sanitize(fileMeta.originalname.toLowerCase().replace(/[\s,;#]+/g, '_'))
 
-  // Prevent overwriting of pasted images
-  if (fileMeta.originalname === 'image.png') {
-    fileMeta.originalname = 'image_' + Date.now() + '.png'
+  // Append timestamp after the filename
+  if (WIKI.config.uploads.appendTimestampToFilename) {
+    const parts = fileMeta.originalname.split('.')
+    const ext = parts.pop()
+    fileMeta.originalname = `${parts.join('.')}_${Date.now()}.${ext}`
   }
 
   // Check if user can upload at path
diff --git a/server/graph/resolvers/site.js b/server/graph/resolvers/site.js
index db538a21..00447839 100644
--- a/server/graph/resolvers/site.js
+++ b/server/graph/resolvers/site.js
@@ -33,7 +33,8 @@ module.exports = {
         uploadMaxFileSize: WIKI.config.uploads.maxFileSize,
         uploadMaxFiles: WIKI.config.uploads.maxFiles,
         uploadScanSVG: WIKI.config.uploads.scanSVG,
-        uploadForceDownload: WIKI.config.uploads.forceDownload
+        uploadForceDownload: WIKI.config.uploads.forceDownload,
+        uploadAppendTimestampToFilename: WIKI.config.uploads.appendTimestampToFilename
       }
     }
   },
@@ -117,7 +118,8 @@ module.exports = {
           maxFileSize: _.get(args, 'uploadMaxFileSize', WIKI.config.uploads.maxFileSize),
           maxFiles: _.get(args, 'uploadMaxFiles', WIKI.config.uploads.maxFiles),
           scanSVG: _.get(args, 'uploadScanSVG', WIKI.config.uploads.scanSVG),
-          forceDownload: _.get(args, 'uploadForceDownload', WIKI.config.uploads.forceDownload)
+          forceDownload: _.get(args, 'uploadForceDownload', WIKI.config.uploads.forceDownload),
+          appendTimestampToFilename: _.get(args, 'uploadAppendTimestampToFilename', WIKI.config.uploads.appendTimestampToFilename)
         }
 
         await WIKI.configSvc.saveToDb(['host', 'title', 'company', 'contentLicense', 'seo', 'logoUrl', 'pageExtensions', 'auth', 'editShortcuts', 'features', 'security', 'uploads'])
diff --git a/server/graph/schemas/site.graphql b/server/graph/schemas/site.graphql
index 4cd36d76..5507bbf6 100644
--- a/server/graph/schemas/site.graphql
+++ b/server/graph/schemas/site.graphql
@@ -64,6 +64,7 @@ type SiteMutation {
     uploadMaxFiles: Int
     uploadScanSVG: Boolean
     uploadForceDownload: Boolean
+    uploadAppendTimestampToFilename: Boolean
 
   ): DefaultResponse @auth(requires: ["manage:system"])
 }
@@ -113,4 +114,5 @@ type SiteConfig {
   uploadMaxFiles: Int
   uploadScanSVG: Boolean
   uploadForceDownload: Boolean
+  uploadAppendTimestampToFilename: Boolean
 }
diff --git a/server/setup.js b/server/setup.js
index 44da308b..c30d0a6a 100644
--- a/server/setup.js
+++ b/server/setup.js
@@ -80,6 +80,9 @@ module.exports = () => {
         tokenExpiration: '30m',
         tokenRenewal: '14d'
       })
+      _.set(WIKI.config, 'upload', {
+        appendTimestampToFilename: false
+      })
       _.set(WIKI.config, 'company', '')
       _.set(WIKI.config, 'features', {
         featurePageRatings: true,