diff --git a/CHANGELOG.md b/CHANGELOG.md
index 0126c9fe4..8ab012294 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -14,6 +14,7 @@
 - Bugfix: Fixed unnecessary saving of windows layout. (#4201)
 - Bugfix: Fixed Reply window missing selection clear behaviour between chat and input box. (#4218)
 - Bugfix: Fixed crash that could occur when changing Tab layout and utilizing multiple windows. (#4248)
+- Bugfix: Fixed text sometimes not pasting properly when image uploader was disabled. (#4246)
 - Dev: Remove protocol from QApplication's Organization Domain (so changed from `https://www.chatterino.com` to `chatterino.com`). (#4256)
 - Dev: Ignore `WM_SHOWWINDOW` hide events, causing fewer attempted rescales. (#4198)
 - Dev: Migrated to C++ 20 (#4252, #4257)
diff --git a/src/widgets/helper/ResizingTextEdit.cpp b/src/widgets/helper/ResizingTextEdit.cpp
index c51458de2..5b0dcd861 100644
--- a/src/widgets/helper/ResizingTextEdit.cpp
+++ b/src/widgets/helper/ResizingTextEdit.cpp
@@ -286,31 +286,34 @@ bool ResizingTextEdit::canInsertFromMimeData(const QMimeData *source) const
 
 void ResizingTextEdit::insertFromMimeData(const QMimeData *source)
 {
-    if (source->hasImage())
+    if (getSettings()->imageUploaderEnabled)
     {
-        this->imagePasted.invoke(source);
-        return;
-    }
-
-    if (source->hasUrls())
-    {
-        bool hasUploadable = false;
-        auto mimeDb = QMimeDatabase();
-        for (const QUrl &url : source->urls())
-        {
-            QMimeType mime = mimeDb.mimeTypeForUrl(url);
-            if (mime.name().startsWith("image"))
-            {
-                hasUploadable = true;
-                break;
-            }
-        }
-
-        if (hasUploadable)
+        if (source->hasImage())
         {
             this->imagePasted.invoke(source);
             return;
         }
+
+        if (source->hasUrls())
+        {
+            bool hasUploadable = false;
+            auto mimeDb = QMimeDatabase();
+            for (const QUrl &url : source->urls())
+            {
+                QMimeType mime = mimeDb.mimeTypeForUrl(url);
+                if (mime.name().startsWith("image"))
+                {
+                    hasUploadable = true;
+                    break;
+                }
+            }
+
+            if (hasUploadable)
+            {
+                this->imagePasted.invoke(source);
+                return;
+            }
+        }
     }
 
     insertPlainText(source->text());