diff --git a/novelwriter/core/coretools.py b/novelwriter/core/coretools.py
index eb113a5d..08b96957 100644
--- a/novelwriter/core/coretools.py
+++ b/novelwriter/core/coretools.py
@@ -348,7 +348,9 @@ class DocSearch:
             rxMatch = rxItt.next()
             pos = rxMatch.capturedStart()
             num = rxMatch.capturedLength()
-            context = text[pos:pos+100].partition("\n")[0]
+            lim = text[:pos].rfind("\n") + 1
+            cut = text[lim:pos].rfind(" ") + lim + 1
+            context = text[cut:cut+100].partition("\n")[0]
             if context:
                 results.append((pos, num, context))
                 count += 1
diff --git a/tests/test_core/test_core_coretools.py b/tests/test_core/test_core_coretools.py
index a0aa86e0..fb5ef0c3 100644
--- a/tests/test_core/test_core_coretools.py
+++ b/tests/test_core/test_core_coretools.py
@@ -439,6 +439,7 @@ def testCoreTools_DocSearch(monkeypatch, mockGUI, fncPath, mockRnd, ipsumText):
         return [(s, n, c.split()[0]) for s, n, c in temp]
 
     # Defaults
+    # assert list(search.iterSearch(project, "Lorem")) == []
     assert pruneResult(search.iterSearch(project, "Lorem"), 2) == [
         (15, 5, "Lorem"), (754, 5, "lorem"), (2056, 5, "lorem,"), (2209, 5, "lorem"),
         (2425, 5, "lorem"), (2840, 5, "lorem."), (3399, 5, "lorem"),
@@ -449,8 +450,8 @@ def testCoreTools_DocSearch(monkeypatch, mockGUI, fncPath, mockRnd, ipsumText):
     assert pruneResult(search.iterSearch(project, "Lor"), 2) == []
     search.setWholeWords(False)
     assert pruneResult(search.iterSearch(project, "Lor"), 2) == [
-        (15, 3, "Lorem"), (29, 3, "lor"), (754, 3, "lorem"), (2056, 3, "lorem,"),
-        (2209, 3, "lorem"), (2425, 3, "lorem"), (2840, 3, "lorem."), (3328, 3, "lor."),
+        (15, 3, "Lorem"), (29, 3, "dolor"), (754, 3, "lorem"), (2056, 3, "lorem,"),
+        (2209, 3, "lorem"), (2425, 3, "lorem"), (2840, 3, "lorem."), (3328, 3, "dolor."),
         (3399, 3, "lorem"),
     ]
 
@@ -458,7 +459,7 @@ def testCoreTools_DocSearch(monkeypatch, mockGUI, fncPath, mockRnd, ipsumText):
     search.setWholeWords(False)
     search.setUserRegEx(True)
     assert pruneResult(search.iterSearch(project, r"Lor\b"), 2) == [
-        (29, 3, "lor"), (3328, 3, "lor."),
+        (29, 3, "dolor"), (3328, 3, "dolor."),
     ]
 
     # Max Results