diff --git a/client/galaxy/scripts/mvc/library/library-foldertoolbar-view.js b/client/galaxy/scripts/mvc/library/library-foldertoolbar-view.js
index f8e85f9ced9..d5f4b1389ce 100644
--- a/client/galaxy/scripts/mvc/library/library-foldertoolbar-view.js
+++ b/client/galaxy/scripts/mvc/library/library-foldertoolbar-view.js
@@ -1382,12 +1382,12 @@ var FolderToolbarView = Backbone.View.extend({
                 "</label>",
                 "</div>",
                 // create new folder button
-                '<button style="display:none;" data-toggle="tooltip" data-placement="top" title="Create New Folder" class="btn btn-default primary-button toolbtn-create-folder add-library-items toolbar-item" type="button">',
+                '<button style="display:none;" data-toggle="tooltip" data-placement="top" title="Create New Folder" class="btn btn-default primary-button toolbtn-create-folder add-library-items add-library-items-folder toolbar-item" type="button">',
                 '<span class="fa fa-plus"></span><span class="fa fa-folder"></span> Create Folder ',
                 "</button>",
                 // add datasets button
                 "<% if(mutiple_add_dataset_options) { %>",
-                '<div class="btn-group add-library-items toolbar-item" style="display:none;">',
+                '<div class="btn-group add-library-items add-library-items-datasets toolbar-item" style="display:none;">',
                 '<button title="Add Datasets to Current Folder" id="" type="button" class="primary-button dropdown-toggle" data-toggle="dropdown">',
                 '<span class="fa fa-plus"></span><span class="fa fa-file"></span> Add Datasets <span class="caret"></span>',
                 "</button>",
@@ -1415,12 +1415,12 @@ var FolderToolbarView = Backbone.View.extend({
                 "<% } %>",
                 // import to history button
                 '<div class="btn-group toolbar-item">',
-                '<button title="Import to history" type="button" class="primary-button dropdown-toggle" data-toggle="dropdown">',
+                '<button title="Import to history" type="button" class="primary-button dropdown-toggle add-to-history" data-toggle="dropdown">',
                 '<span class="fa fa-book"></span> To History <span class="caret"></span>',
                 "</button>",
                 '<ul class="dropdown-menu" role="menu">',
-                '<li><a href="" class="toolbtn-bulk-import">as Datasets</a></li>',
-                '<li><a href="" class="toolbtn-collection-import">as a Collection</a></li>',
+                '<li><a href="" class="toolbtn-bulk-import add-to-history-datasets">as Datasets</a></li>',
+                '<li><a href="" class="toolbtn-collection-import add-to-history-collection">as a Collection</a></li>',
                 "</ul>",
                 "</div>",
                 // download button
@@ -1828,13 +1828,13 @@ var FolderToolbarView = Backbone.View.extend({
                 "<h4>Which datasets?</h4>",
                 '<form class="form-inline">',
                 '<label class="radio-inline">',
-                '<input type="radio" name="radio_elements" id="selection_radio" value="selection" <% if (!selected_datasets) { %> disabled <% } %> > current selection',
+                '<input type="radio" name="radio_elements" id="selection_radio" value="selection" <% if (!selected_datasets) { %> disabled <% } else { %> checked <% } %> > current selection',
                 "<% if (selected_datasets) { %>",
                 " (<%- selected_datasets %>)",
                 "<% } %>",
                 "</label>",
                 '<label class="radio-inline">',
-                '<input type="radio" name="radio_elements" id="folder_radio" value="folder"> all datasets in current folder',
+                '<input type="radio" name="radio_elements" id="folder_radio" value="folder" <% if (!selected_datasets) { %> checked <% } %> > all datasets in current folder',
                 "</label>",
                 "</form>",
                 "</div>",
diff --git a/test/galaxy_selenium/navigates_galaxy.py b/test/galaxy_selenium/navigates_galaxy.py
index 1d20c179d9a..0ddfc8ad4cf 100644
--- a/test/galaxy_selenium/navigates_galaxy.py
+++ b/test/galaxy_selenium/navigates_galaxy.py
@@ -612,6 +612,11 @@ class NavigatesGalaxy(HasDriver):
         self.components.masthead.libraries.wait_for_and_click()
         self.components.libraries.selector.wait_for_visible()
 
+    def libraries_open_with_name(self, name):
+        self.libraries_open()
+        self.libraries_index_search_for(name)
+        self.libraries_index_table_elements()[0].find_element_by_css_selector("td a").click()
+
     @retry_during_transitions
     def libraries_index_table_elements(self):
         container = self.wait_for_selector_visible(".library_container")
@@ -681,6 +686,26 @@ class NavigatesGalaxy(HasDriver):
         self.wait_for_visible(self.navigation.libraries.folder.selectors.add_items_menu)
         self.wait_for_and_click(self.navigation.libraries.folder.labels.from_path)
 
+    def libraries_dataset_import_from_history_select(self, to_select_items):
+        self.wait_for_visible(self.navigation.libraries.folder.selectors.import_history_content)
+        history_elements = self.find_elements(self.navigation.libraries.folder.selectors.import_history_contents_items)
+        for to_select_item in to_select_items:
+            found = False
+            for history_element in history_elements:
+                if to_select_item in history_element.text:
+                    history_element.find_element_by_css_selector("input").click()
+                    found = True
+                    break
+
+            if not found:
+                raise Exception("Failed to find history item [%s] to select" % to_select_item)
+
+    def libraries_dataset_import_from_history_click_ok(self, wait=True):
+        self.wait_for_and_click(self.navigation.libraries.folder.selectors.import_datasets_ok_button)
+        if wait:
+            # Let the progress bar disappear...
+            self.wait_for_absent_or_hidden(self.navigation.libraries.folder.selectors.import_progress_bar)
+
     def libraries_table_elements(self):
         tbody_element = self.wait_for_selector_visible("#folder_list_body")
         return tbody_element.find_elements_by_css_selector("tr")[1:]
diff --git a/test/galaxy_selenium/navigation.yml b/test/galaxy_selenium/navigation.yml
index 007f8593476..22b6979bc70 100644
--- a/test/galaxy_selenium/navigation.yml
+++ b/test/galaxy_selenium/navigation.yml
@@ -236,14 +236,14 @@ libraries:
 
   folder:
     selectors:
-      # There needs to a different class or ID on the dataset button, this isn't
-      # a good selector for that button since .add-library-items also applies to
-      # folder (but it is a button.add-library-items instead).
-      add_items_button: 'div.add-library-items'
-      add_items_menu: 'div.add-library-items .dropdown-menu'
-      add_items_options: 'div.add-library-items .dropdown-menu li a'
+      add_items_button: '.add-library-items-datasets'
+      add_items_menu: '.add-library-items-datasets .dropdown-menu'
+      add_items_options: '.add-library-items-datasets .dropdown-menu li a'
 
-      # TODO: Most of these are very good selectors but the same DOM elements
+      add_to_history: '.add-to-history'
+      add_to_history_datasets: '.add-to-history-datasets'
+      add_to_history_collection: '.add-to-history-collection'
+      # TODO: Most of these aren't very good selectors but the same DOM elements
       # are reused without adding specific classes, IDs, or roles to anything.
       import_modal: '.modal'
       import_datasets_ok_button: '.modal-footer .buttons #button-0'
@@ -252,6 +252,7 @@ libraries:
       import_history_content: '.library_selected_history_content'
       import_history_contents_items: '.library_selected_history_content ul li'
       import_from_path_textarea: '#import_paths'
+      select_all: '#select-all-checkboxes'
 
     labels:
       from_history: 'from History'
diff --git a/test/selenium_tests/test_library_contents.py b/test/selenium_tests/test_library_contents.py
index 570de3ca9a9..0481af9cc60 100644
--- a/test/selenium_tests/test_library_contents.py
+++ b/test/selenium_tests/test_library_contents.py
@@ -31,16 +31,11 @@ class LibraryContentsTestCase(SeleniumTestCase):
         self.wait_for_absent_or_hidden(self.navigation.libraries.folder.selectors.import_modal)
 
         self.libraries_dataset_import_from_history()
-        self.wait_for_visible(self.navigation.libraries.folder.selectors.import_history_content)
-        history_elements = self.find_elements(self.navigation.libraries.folder.selectors.import_history_contents_items)
-        assert "1.txt" in history_elements[0].text
-        history_elements[0].find_element_by_css_selector("input").click()
+        self.libraries_dataset_import_from_history_select(["1.txt"])
         # Add
         self.sleep_for(self.wait_types.UX_RENDER)
         self.screenshot("libraries_dataset_import")
-        self.wait_for_and_click(self.navigation.libraries.folder.selectors.import_datasets_ok_button)
-        # Let the progress bar disappear...
-        self.wait_for_absent_or_hidden(self.navigation.libraries.folder.selectors.import_progress_bar)
+        self.libraries_dataset_import_from_history_click_ok()
         self._assert_num_displayed_items_is(1)
 
     # Fine test locally but the upload doesn't work in Docker compose. I'd think
@@ -103,6 +98,4 @@ class LibraryContentsTestCase(SeleniumTestCase):
         self.libraries_open()
         self.name = self._get_random_name(prefix="testcontents")
         self.libraries_index_create(self.name)
-        self.wait_for_overlays_cleared()
-        self.libraries_index_search_for(self.name)
-        self.libraries_index_table_elements()[0].find_element_by_css_selector("td a").click()
+        self.libraries_open_with_name(self.name)
diff --git a/test/selenium_tests/test_library_to_collections.py b/test/selenium_tests/test_library_to_collections.py
new file mode 100644
index 00000000000..b2314f6db1f
--- /dev/null
+++ b/test/selenium_tests/test_library_to_collections.py
@@ -0,0 +1,46 @@
+from .framework import (
+    selenium_test,
+    SharedStateSeleniumTestCase,
+)
+
+
+class LibraryToCollectionsTestCase(SharedStateSeleniumTestCase):
+
+    requires_admin = True
+
+    @selenium_test
+    def test_list_creation(self):
+        self.admin_login()
+        self.history_panel_create_new_with_name("new_history_for_library_list")
+        self.libraries_open_with_name(self.name)
+        self.sleep_for(self.wait_types.UX_RENDER)
+        self.components.libraries.folder.select_all.wait_for_and_click()
+        self.components.libraries.folder.add_to_history.wait_for_and_click()
+        self.screenshot("libraries_add_to_history_menu")
+        self.components.libraries.folder.add_to_history_collection.wait_for_and_click()
+        self.sleep_for(self.wait_types.UX_RENDER)
+        self.screenshot("libraries_to_collection_landing")
+        self.components.libraries.folder.import_datasets_ok_button.wait_for_and_click()
+
+        self.collection_builder_set_name("my cool list")
+        self.collection_builder_create()
+        self.home()
+        self.history_panel_wait_for_hid_ok(3)
+
+    def setup_shared_state(self):
+        self.admin_login()
+        self.perform_upload(self.get_filename("1.bed"))
+        self.wait_for_history()
+        self.perform_upload(self.get_filename("2.bed"))
+        self.wait_for_history()
+
+        self.name = self._get_random_name(prefix="testcontents")
+
+        self.libraries_open()
+        self.libraries_index_create(self.name)
+        self.libraries_open_with_name(self.name)
+
+        self.libraries_dataset_import_from_history()
+        self.libraries_dataset_import_from_history_select(["1.bed", "2.bed"])
+        self.sleep_for(self.wait_types.UX_RENDER)
+        self.libraries_dataset_import_from_history_click_ok()