diff --git a/Changelog.md b/Changelog.md
index 56c7a8ea..53a5b1dd 100644
--- a/Changelog.md
+++ b/Changelog.md
@@ -17,6 +17,7 @@ This changelog should be updated as part of a PR if the work is worth noting (mo
 - [#741](https://github.com/timescale/timescaledb-toolkit/pull/741): Stabilize `approx_count_distinct`
 
 #### Other notable changes
+- [#743](https://github.com/timescale/timescaledb-toolkit/pull/743): Remove support for direct upgrades from toolkit versions more than 1 year old. Toolkit versions 1.4.x and 1.5.x will have to upgrade to an intermediate version before upgrading to 1.16.0.
 - [#744](https://github.com/timescale/timescaledb-toolkit/pull/744): Fix nightly CI failures from building TimescaleDB on Enterprise Linux
 
 #### Shout-outs
diff --git a/extension/timescaledb_toolkit.control b/extension/timescaledb_toolkit.control
index 0ed8b240..eac7cbb7 100644
--- a/extension/timescaledb_toolkit.control
+++ b/extension/timescaledb_toolkit.control
@@ -5,4 +5,4 @@ superuser = false
 module_pathname = '$libdir/timescaledb_toolkit' # only for testing, will be removed for real installs
 # comma-separated list of previous versions this version can be upgraded from
 # directly. This is used to generate upgrade scripts.
-# upgradeable_from = '1.4, 1.5, 1.5.1, 1.5.2, 1.6.0, 1.7.0, 1.8.0, 1.10.0-dev, 1.10.1, 1.11.0, 1.12.0, 1.12.1, 1.13.0, 1.13.1, 1.14.0, 1.15.0'
+# upgradeable_from = '1.6.0, 1.7.0, 1.8.0, 1.10.0-dev, 1.10.1, 1.11.0, 1.12.0, 1.12.1, 1.13.0, 1.13.1, 1.14.0, 1.15.0'