diff --git a/ChangeLog b/ChangeLog
index f15e415ec..0b864c290 100644
--- a/ChangeLog
+++ b/ChangeLog
@@ -189,6 +189,8 @@
           question marks, and braces (thanks to Ralph Bean).
 - TW-1468 Filtering for project and description has issues (thanks to Richard
           Boß).
+- TW-1469 Case-insensitive searching broken on Cygwin (thanks to Richard
+          Boß).
 - Added new holidays.xy-XY.rc definition files
 - Removed deprecated 'echo.command' setting, in favor of the 'header' and
   'affected' verbosity tokens.
diff --git a/NEWS b/NEWS
index 3a1375679..a8446158f 100644
--- a/NEWS
+++ b/NEWS
@@ -78,6 +78,8 @@ Removed features in 2.4.0
 
 Known Issues
 
+  - On Cygwin, case-insensitive regex searches are broken. The default is
+    now case-sensitive for Cygwin only.
   - https://bug.tasktools.org
 
 Taskwarrior has been built and tested on the following configurations:
diff --git a/src/Config.cpp b/src/Config.cpp
index 4ccb4bb8b..3d82d0b06 100644
--- a/src/Config.cpp
+++ b/src/Config.cpp
@@ -90,7 +90,11 @@ std::string Config::_defaults =
   "column.padding=1                               # Spaces between each column in a report\n"
   "bulk=3                                         # 3 or more tasks considered a bulk change and is confirmed\n"
   "nag=You have more urgent tasks.                # Nag message to keep you honest\n"                      // TODO
+#ifdef CYGWIN
+  "search.case.sensitive=no                       # Case-insensitive regex searches are broken under Cygwin\n"
+#else
   "search.case.sensitive=yes                      # Setting to no allows case insensitive searches\n"
+#endif
   "active.indicator=*                             # What to show as an active task indicator\n"
   "tag.indicator=+                                # What to show as a tag indicator\n"
   "dependency.indicator=D                         # What to show as a dependency indicator\n"