diff --git a/src/calibre/gui2/tweak_book/boss.py b/src/calibre/gui2/tweak_book/boss.py
index de605790fb..c5fbfeccf5 100644
--- a/src/calibre/gui2/tweak_book/boss.py
+++ b/src/calibre/gui2/tweak_book/boss.py
@@ -643,9 +643,9 @@ class Boss(QObject):
                     ed.insert_image(href)
             elif action[0] == 'insert_hyperlink':
                 self.commit_all_editors_to_container()
-                d = InsertLink(current_container(), edname, parent=self.gui)
+                d = InsertLink(current_container(), edname, initial_text=ed.get_smart_selection(), parent=self.gui)
                 if d.exec_() == d.Accepted:
-                    ed.insert_hyperlink(d.href)
+                    ed.insert_hyperlink(d.href, d.text)
             else:
                 ed.action_triggered(action)
 
diff --git a/src/calibre/gui2/tweak_book/editor/smart/__init__.py b/src/calibre/gui2/tweak_book/editor/smart/__init__.py
index 7cb00ca997..b13c22032a 100644
--- a/src/calibre/gui2/tweak_book/editor/smart/__init__.py
+++ b/src/calibre/gui2/tweak_book/editor/smart/__init__.py
@@ -14,3 +14,6 @@ class NullSmarts(object):
     def get_extra_selections(self, editor):
         return ()
 
+    def get_smart_selection(self, editor, update=True):
+        return editor.selected_text
+
diff --git a/src/calibre/gui2/tweak_book/editor/smart/html.py b/src/calibre/gui2/tweak_book/editor/smart/html.py
index bd4a5b568f..a0b2a1ba77 100644
--- a/src/calibre/gui2/tweak_book/editor/smart/html.py
+++ b/src/calibre/gui2/tweak_book/editor/smart/html.py
@@ -129,7 +129,7 @@ def rename_tag(cursor, opening_tag, closing_tag, new_name, insert=False):
     cursor.insertText(text)
     cursor.endEditBlock()
 
-def ensure_not_within_tag_definition(cursor):
+def ensure_not_within_tag_definition(cursor, forward=True):
     ''' Ensure the cursor is not inside a tag definition <>. Returns True iff the cursor was moved. '''
     block, offset = cursor.block(), cursor.positionInBlock()
     b, boundary = next_tag_boundary(block, offset, forward=False)
@@ -137,10 +137,15 @@ def ensure_not_within_tag_definition(cursor):
         return False
     if boundary.is_start:
         # We are inside a tag
-        block, boundary = next_tag_boundary(block, offset)
-        if block is not None:
-            cursor.setPosition(block.position() + boundary.offset + 1)
+        if forward:
+            block, boundary = next_tag_boundary(block, offset)
+            if block is not None:
+                cursor.setPosition(block.position() + boundary.offset + 1)
+                return True
+        else:
+            cursor.setPosition(b.position() + boundary.offset)
             return True
+
     return False
 
 class HTMLSmarts(NullSmarts):
@@ -195,7 +200,27 @@ class HTMLSmarts(NullSmarts):
             return error_dialog(editor, _('No found'), _(
                 'No suitable block level tag was found to rename'), show=True)
 
-    def insert_hyperlink(self, editor, target):
+    def get_smart_selection(self, editor, update=True):
+        cursor = editor.textCursor()
+        if not cursor.hasSelection():
+            return ''
+        left = min(cursor.anchor(), cursor.position())
+        right = max(cursor.anchor(), cursor.position())
+
+        cursor.setPosition(left)
+        ensure_not_within_tag_definition(cursor)
+        left = cursor.position()
+
+        cursor.setPosition(right)
+        ensure_not_within_tag_definition(cursor, forward=False)
+        right = cursor.position()
+
+        cursor.setPosition(left), cursor.setPosition(right, cursor.KeepAnchor)
+        if update:
+            editor.setTextCursor(cursor)
+        return editor.selected_text_from_cursor(cursor)
+
+    def insert_hyperlink(self, editor, target, text):
         c = editor.textCursor()
         if c.hasSelection():
             c.insertText('')  # delete any existing selected text
@@ -204,4 +229,6 @@ class HTMLSmarts(NullSmarts):
         p = c.position()
         c.insertText('</a>')
         c.setPosition(p)  # ensure cursor is positioned inside the newly created tag
+        if text:
+            c.insertText(text)
         editor.setTextCursor(c)
diff --git a/src/calibre/gui2/tweak_book/editor/text.py b/src/calibre/gui2/tweak_book/editor/text.py
index cccb274c97..d310906ea4 100644
--- a/src/calibre/gui2/tweak_book/editor/text.py
+++ b/src/calibre/gui2/tweak_book/editor/text.py
@@ -101,9 +101,12 @@ class PlainTextEdit(QPlainTextEdit):
         self.copy()
         self.textCursor().removeSelectedText()
 
+    def selected_text_from_cursor(self, cursor):
+        return unicodedata.normalize('NFC', unicode(cursor.selectedText()).replace(PARAGRAPH_SEPARATOR, '\n').rstrip('\0'))
+
     @property
     def selected_text(self):
-        return unicodedata.normalize('NFC', unicode(self.textCursor().selectedText()).replace(PARAGRAPH_SEPARATOR, '\n').rstrip('\0'))
+        return self.selected_text_from_cursor(self.textCursor())
 
     def selection_changed(self):
         # Workaround Qt replacing nbsp with normal spaces on copy
@@ -602,9 +605,9 @@ class TextEdit(PlainTextEdit):
             c.setPosition(left + len(text), c.KeepAnchor)
         self.setTextCursor(c)
 
-    def insert_hyperlink(self, target):
+    def insert_hyperlink(self, target, text):
         if hasattr(self.smarts, 'insert_hyperlink'):
-            self.smarts.insert_hyperlink(self, target)
+            self.smarts.insert_hyperlink(self, target, text)
 
     def keyPressEvent(self, ev):
         if ev.key() == Qt.Key_X and ev.modifiers() == Qt.AltModifier:
diff --git a/src/calibre/gui2/tweak_book/editor/widget.py b/src/calibre/gui2/tweak_book/editor/widget.py
index d4c7de956a..81a54d17a9 100644
--- a/src/calibre/gui2/tweak_book/editor/widget.py
+++ b/src/calibre/gui2/tweak_book/editor/widget.py
@@ -144,8 +144,8 @@ class Editor(QMainWindow):
     def insert_image(self, href):
         self.editor.insert_image(href)
 
-    def insert_hyperlink(self, href):
-        self.editor.insert_hyperlink(href)
+    def insert_hyperlink(self, href, text):
+        self.editor.insert_hyperlink(href, text)
 
     def undo(self):
         self.editor.undo()
@@ -157,6 +157,9 @@ class Editor(QMainWindow):
     def selected_text(self):
         return self.editor.selected_text
 
+    def get_smart_selection(self, update=True):
+        return self.editor.smarts.get_smart_selection(self.editor, update=update)
+
     # Search and replace {{{
     def mark_selected_text(self):
         self.editor.mark_selected_text()
diff --git a/src/calibre/gui2/tweak_book/widgets.py b/src/calibre/gui2/tweak_book/widgets.py
index 445eaf493a..0ca22d1832 100644
--- a/src/calibre/gui2/tweak_book/widgets.py
+++ b/src/calibre/gui2/tweak_book/widgets.py
@@ -537,9 +537,10 @@ def create_filterable_names_list(names, filter_text=None, parent=None):
 # Insert Link {{{
 class InsertLink(Dialog):
 
-    def __init__(self, container, source_name, parent=None):
+    def __init__(self, container, source_name, initial_text=None, parent=None):
         self.container = container
         self.source_name = source_name
+        self.initial_text = initial_text
         Dialog.__init__(self, _('Insert Hyperlink'), 'insert-hyperlink', parent=parent)
         self.anchor_cache = {}
 
@@ -573,14 +574,18 @@ class InsertLink(Dialog):
         fnl.addWidget(la), fnl.addWidget(f), fnl.addWidget(fn)
         h.addLayout(fnl), h.setStretch(1, 1)
 
-        self.tl = tl = QHBoxLayout()
-        self.la3 = la = QLabel(_('&Target:'))
-        tl.addWidget(la)
+        self.tl = tl = QFormLayout()
         self.target = t = QLineEdit(self)
-        la.setBuddy(t)
-        tl.addWidget(t)
+        t.setPlaceholderText(_('The destination (href) for the link'))
+        tl.addRow(_('&Target:'), t)
         l.addLayout(tl)
 
+        self.text_edit = t = QLineEdit(self)
+        la.setBuddy(t)
+        tl.addRow(_('Te&xt:'), t)
+        t.setText(self.initial_text or '')
+        t.setPlaceholderText(_('The (optional) text for the link'))
+
         l.addWidget(self.bb)
 
     def selected_file_changed(self, *args):
@@ -622,6 +627,10 @@ class InsertLink(Dialog):
     def href(self):
         return unicode(self.target.text()).strip()
 
+    @property
+    def text(self):
+        return unicode(self.text_edit.text()).strip()
+
     @classmethod
     def test(cls):
         import sys
@@ -629,7 +638,7 @@ class InsertLink(Dialog):
         c = get_container(sys.argv[-1], tweak_mode=True)
         d = cls(c, next(c.spine_names)[0])
         if d.exec_() == d.Accepted:
-            print (d.href)
+            print (d.href, d.text)
 
 # }}}