diff --git a/CHANGELOG.md b/CHANGELOG.md
index 82be7d5a..0b4d89d1 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,7 @@
 
 ## Unversioned
 
+- Minor: Delete all but the last 5 crashdumps on application start. (#4392)
 - Dev: Add capability to build Chatterino with Qt6. (#4393)
 - Dev: Fix homebrew update action. (#4394)
 
diff --git a/src/RunGui.cpp b/src/RunGui.cpp
index fdf557e6..49c800a6 100644
--- a/src/RunGui.cpp
+++ b/src/RunGui.cpp
@@ -185,6 +185,38 @@ namespace {
         }
         qCDebug(chatterinoCache) << "Deleted" << deletedCount << "files";
     }
+
+    // We delete all but the five most recent crashdumps. This strategy may be
+    // improved in the future.
+    void clearCrashes(QDir dir)
+    {
+        // crashpad crashdumps are stored inside the Crashes/report directory
+        if (!dir.cd("reports"))
+        {
+            // no reports directory exists = no files to delete
+            return;
+        }
+
+        dir.setNameFilters({"*.dmp"});
+
+        size_t deletedCount = 0;
+        // TODO: use std::views::drop once supported by all compilers
+        size_t filesToSkip = 5;
+        for (auto &&info : dir.entryInfoList(QDir::Files, QDir::Time))
+        {
+            if (filesToSkip > 0)
+            {
+                filesToSkip--;
+                continue;
+            }
+
+            if (QFile(info.absoluteFilePath()).remove())
+            {
+                deletedCount++;
+            }
+        }
+        qCDebug(chatterinoApp) << "Deleted" << deletedCount << "crashdumps";
+    }
 }  // namespace
 
 void runGui(QApplication &a, Paths &paths, Settings &settings)
@@ -215,10 +247,15 @@ void runGui(QApplication &a, Paths &paths, Settings &settings)
     });
 
     // Clear the cache 1 minute after start.
-    QTimer::singleShot(60 * 1000, [cachePath = paths.cacheDirectory()] {
+    QTimer::singleShot(60 * 1000, [cachePath = paths.cacheDirectory(),
+                                   crashDirectory = paths.crashdumpDirectory] {
         QtConcurrent::run([cachePath]() {
             clearCache(cachePath);
         });
+
+        QtConcurrent::run([crashDirectory]() {
+            clearCrashes(crashDirectory);
+        });
     });
 
     chatterino::NetworkManager::init();