diff --git a/src/server/src/extensions/clipboard/clipboard-extension.cpp b/src/server/src/extensions/clipboard/clipboard-extension.cpp
index a1996424c..1fd5d537f 100644
--- a/src/server/src/extensions/clipboard/clipboard-extension.cpp
+++ b/src/server/src/extensions/clipboard/clipboard-extension.cpp
@@ -6,6 +6,8 @@
 #include "extensions/clipboard/clipboard-history-command.hpp"
 #include "service-registry.hpp"
 
+bool ClipboardExtension::preservePinnedOnClear = false;
+
 class ClipboardClearCommand : public BuiltinCallbackCommand {
   QString id() const override { return "clear"; }
   QString name() const override { return "Clear Current Clipboard Data"; }
@@ -38,10 +40,11 @@ class ClearClipboardHistoryCommand : public BuiltinCallbackCommand {
     auto ctx = ctrl->context();
     auto clipman = ctx->services->clipman();
     auto toast = ctx->services->toastService();
+    bool preservePinned = ClipboardExtension::preservePinnedOnClear;
 
     ctx->navigation->confirmAlert("Are you sure?", "Your clipboard history will be gone forever :(",
-                                  [clipman, toast]() {
-                                    if (!clipman->removeAllSelections()) {
+                                  [clipman, toast, preservePinned]() {
+                                    if (!clipman->removeAllSelections(preservePinned)) {
                                       toast->failure("Failed to clear clipboard history");
                                       return;
                                     }
@@ -60,8 +63,9 @@ ClipboardExtension::ClipboardExtension() {
 void ClipboardExtension::initialized(const QJsonObject &preferences) const {
   auto clipman = ServiceRegistry::instance()->clipman();
   bool const eraseOnStartup = preferences.value("eraseOnStartup").toBool();
+  preservePinnedOnClear = preferences.value("preservePinnedOnClear").toBool(false);
 
-  if (eraseOnStartup) { clipman->removeAllSelections(); }
+  if (eraseOnStartup) { clipman->removeAllSelections(preservePinnedOnClear); }
 }
 
 void ClipboardExtension::preferenceValuesChanged(const QJsonObject &value) const {
@@ -70,6 +74,7 @@ void ClipboardExtension::preferenceValuesChanged(const QJsonObject &value) const
   clipman->setMonitoring(value.value("monitoring").toBool());
   clipman->setEncryption(value.value("encryption").toBool());
   clipman->setIgnorePasswords(value.value("ignorePasswords").toBool());
+  preservePinnedOnClear = value.value("preservePinnedOnClear").toBool();
 }
 
 std::vector<Preference> ClipboardExtension::preferences() const {
@@ -77,6 +82,7 @@ std::vector<Preference> ClipboardExtension::preferences() const {
   auto monitoring = Preference::makeCheckbox("monitoring");
   auto eraseOnStartup = Preference::makeCheckbox("eraseOnStartup");
   auto ignorePasswords = Preference::makeCheckbox("ignorePasswords");
+  auto preservePinnedOnClear = Preference::makeCheckbox("preservePinnedOnClear");
 
   eraseOnStartup.setTitle("Erase on startup");
   eraseOnStartup.setDescription("Erase clipboard history every time the vicinae server is started");
@@ -100,5 +106,9 @@ std::vector<Preference> ClipboardExtension::preferences() const {
                             "performed while this is turned off will not be recorded.");
   monitoring.setDefaultValue(true);
 
-  return {monitoring, ignorePasswords, eraseOnStartup, encryption};
+  preservePinnedOnClear.setTitle("Preserve pinned on clear");
+  preservePinnedOnClear.setDescription("Keep pinned items when clearing clipboard history");
+  preservePinnedOnClear.setDefaultValue(false);
+
+  return {monitoring, ignorePasswords, eraseOnStartup, encryption, preservePinnedOnClear};
 }
diff --git a/src/server/src/extensions/clipboard/clipboard-extension.hpp b/src/server/src/extensions/clipboard/clipboard-extension.hpp
index 9a8af08d7..5868db2b9 100644
--- a/src/server/src/extensions/clipboard/clipboard-extension.hpp
+++ b/src/server/src/extensions/clipboard/clipboard-extension.hpp
@@ -18,4 +18,6 @@ class ClipboardExtension : public BuiltinCommandRepository {
   void preferenceValuesChanged(const QJsonObject &value) const override;
 
   ClipboardExtension();
+
+  static bool preservePinnedOnClear;
 };
diff --git a/src/server/src/extensions/clipboard/history/clipboard-history-actions.hpp b/src/server/src/extensions/clipboard/history/clipboard-history-actions.hpp
index fece4ec52..e71e8d505 100644
--- a/src/server/src/extensions/clipboard/history/clipboard-history-actions.hpp
+++ b/src/server/src/extensions/clipboard/history/clipboard-history-actions.hpp
@@ -5,6 +5,7 @@
 #include "services/clipboard/clipboard-service.hpp"
 #include "services/toast/toast-service.hpp"
 #include "ui/alert/alert.hpp"
+#include "extensions/clipboard/clipboard-extension.hpp"
 
 class PasteClipboardSelection : public PasteToFocusedWindowAction {
   QString m_id;
@@ -99,7 +100,8 @@ class RemoveAllSelectionsAction : public AbstractAction {
     alert->setConfirmCallback([ctx]() {
       auto toast = ctx->services->toastService();
       auto clipman = ctx->services->clipman();
-      if (clipman->removeAllSelections()) {
+      bool preservePinned = ClipboardExtension::preservePinnedOnClear;
+      if (clipman->removeAllSelections(preservePinned)) {
         toast->success("All selections were removed");
       } else {
         toast->failure("Failed to remove all selections");
diff --git a/src/server/src/services/clipboard/clipboard-db.cpp b/src/server/src/services/clipboard/clipboard-db.cpp
index add562e7f..aa28e2af6 100644
--- a/src/server/src/services/clipboard/clipboard-db.cpp
+++ b/src/server/src/services/clipboard/clipboard-db.cpp
@@ -191,6 +191,37 @@ bool ClipboardDatabase::removeAll() {
          query.exec("DELETE FROM selection");
 }
 
+bool ClipboardDatabase::removeAll(bool preservePinned) {
+  QSqlQuery query(m_db);
+
+  if (preservePinned) {
+    return query.exec("DELETE FROM selection_fts") &&
+           query.exec("DELETE FROM data_offer WHERE selection_id IN (SELECT id FROM selection WHERE "
+                      "pinned_at IS NULL)") &&
+           query.exec("DELETE FROM selection WHERE pinned_at IS NULL");
+  }
+
+  return removeAll();
+}
+
+std::vector<QString> ClipboardDatabase::getOfferIdsToDelete(bool preservePinned) {
+  std::vector<QString> offerIds;
+  QSqlQuery query(m_db);
+
+  if (preservePinned) {
+    query.exec(
+        "SELECT id FROM data_offer WHERE selection_id IN (SELECT id FROM selection WHERE pinned_at IS NULL)");
+  } else {
+    query.exec("SELECT id FROM data_offer");
+  }
+
+  while (query.next()) {
+    offerIds.emplace_back(query.value(0).toString());
+  }
+
+  return offerIds;
+}
+
 std::vector<QString> ClipboardDatabase::removeSelection(const QString &selectionId) {
   if (!m_db.transaction()) { return {}; }
 
diff --git a/src/server/src/services/clipboard/clipboard-db.hpp b/src/server/src/services/clipboard/clipboard-db.hpp
index 91baa5114..3e66230a5 100644
--- a/src/server/src/services/clipboard/clipboard-db.hpp
+++ b/src/server/src/services/clipboard/clipboard-db.hpp
@@ -91,6 +91,8 @@ class ClipboardDatabase {
                                                  const ClipboardListSettings &opts = {}) const;
 
   bool removeAll();
+  bool removeAll(bool preservePinned);
+  std::vector<QString> getOfferIdsToDelete(bool preservePinned);
 
   bool setKeywords(const QString &id, const QString &keywords);
   std::optional<QString> retrieveKeywords(const QString &id);
diff --git a/src/server/src/services/clipboard/clipboard-service.cpp b/src/server/src/services/clipboard/clipboard-service.cpp
index d0c6b35e4..d5ab495ee 100644
--- a/src/server/src/services/clipboard/clipboard-service.cpp
+++ b/src/server/src/services/clipboard/clipboard-service.cpp
@@ -598,6 +598,30 @@ bool ClipboardService::removeAllSelections() {
   return true;
 }
 
+bool ClipboardService::removeAllSelections(bool preservePinned) {
+  ClipboardDatabase db;
+
+  auto offerIds = db.getOfferIdsToDelete(preservePinned);
+
+  if (!db.removeAll(preservePinned)) {
+    qWarning() << "Failed to remove clipboard selections";
+    return false;
+  }
+
+  if (!preservePinned) {
+    fs::remove_all(m_dataDir);
+    fs::create_directories(m_dataDir);
+  } else {
+    for (const auto &offerId : offerIds) {
+      fs::remove(m_dataDir / offerId.toStdString());
+    }
+  }
+
+  emit allSelectionsRemoved();
+
+  return true;
+}
+
 AbstractClipboardServer *ClipboardService::clipboardServer() const { return m_clipboardServer.get(); }
 
 ClipboardService::ClipboardService(const std::filesystem::path &path) {
diff --git a/src/server/src/services/clipboard/clipboard-service.hpp b/src/server/src/services/clipboard/clipboard-service.hpp
index de490c0b4..4a1f7bfb9 100644
--- a/src/server/src/services/clipboard/clipboard-service.hpp
+++ b/src/server/src/services/clipboard/clipboard-service.hpp
@@ -79,6 +79,7 @@ class ClipboardService : public QObject, public NonCopyable {
   static Clipboard::ReadContent readContent();
 
   bool removeAllSelections();
+  bool removeAllSelections(bool preservePinned);
 
   std::optional<QString> retrieveKeywords(const QString &id);
   bool setKeywords(const QString &id, const QString &keywords);