diff --git a/docs/source/release_notes.rst b/docs/source/release_notes.rst
index d8936f6c..cf4d867a 100644
--- a/docs/source/release_notes.rst
+++ b/docs/source/release_notes.rst
@@ -5,6 +5,10 @@ Development - |version|
 -----------------------
 .. *Release Date: MMM. DD, YYYY*
 
+* Fix a bug where extending an access opportunity window across a generation seam
+  could leave the satellite's ``opportunities`` list out of close-time order, which
+  corrupted ``bisect``-based opportunity lookups. See issue #205.
+
 Version 1.3.0
 -------------
 *Release Date: May. 19, 2026*
diff --git a/src/bsk_rl/sats/access_satellite.py b/src/bsk_rl/sats/access_satellite.py
index 6231e348..e4972d9f 100644
--- a/src/bsk_rl/sats/access_satellite.py
+++ b/src/bsk_rl/sats/access_satellite.py
@@ -288,13 +288,25 @@ def _add_window(
                 check all windows for merges.
         """
         if new_window[0] == merge_time or merge_time is None:
-            for opportunity in self.opportunities:
+            for i, opportunity in enumerate(self.opportunities):
                 if (
                     opportunity["type"] == type
                     and opportunity["object"] == object
                     and opportunity["window"][1] == new_window[0]
                 ):
+                    # Extending the close time changes the opportunity's sort
+                    # position, so re-insert it to keep opportunities ordered by
+                    # close time (see issue #205). Remove by index rather than
+                    # value: opportunity dicts hold r_LP_P as a numpy array, so
+                    # list.remove would compare arrays and raise on their
+                    # ambiguous truth value.
+                    del self.opportunities[i]
                     opportunity["window"] = (opportunity["window"][0], new_window[1])
+                    bisect.insort(
+                        self.opportunities,
+                        opportunity,
+                        key=lambda x: x["window"][1],
+                    )
                     return
         bisect.insort(
             self.opportunities,
diff --git a/tests/unittest/sats/test_access_satellite.py b/tests/unittest/sats/test_access_satellite.py
index d20f004a..78e82ee6 100644
--- a/tests/unittest/sats/test_access_satellite.py
+++ b/tests/unittest/sats/test_access_satellite.py
@@ -237,6 +237,37 @@ def test_add_window(self, merge_time, tgt, window, expected_window):
         )
         assert expected_window in sat.opportunities_dict()[tgt]
 
+    def test_add_window_merge_keeps_sorted(self):
+        # Regression test for issue #205: extending a window across a generation
+        # seam via the merge path must keep opportunities sorted by close time.
+        sat = self.make_sat()
+        # Segment 1 left tgt0 truncated at the seam (close time 30). Seed with
+        # r_LP_P as a numpy array to match how _add_window stores opportunities.
+        sat.opportunities = [
+            dict(
+                object=self.tgt0,
+                window=(5.0, 30.0),
+                type="target",
+                r_LP_P=np.zeros(3),
+            ),
+        ]
+        # Segment 2 generates windows starting at the seam (merge_time=30).
+        # Insert opportunities that close after the seam but before tgt0's
+        # true close time, then extend tgt0 across the seam.
+        sat._add_window(
+            self.tgt1, (31.0, 35.0), merge_time=30.0, type="target", r_LP_P=np.zeros(3)
+        )
+        sat._add_window(
+            self.tgt2, (33.0, 40.0), merge_time=30.0, type="target", r_LP_P=np.zeros(3)
+        )
+        sat._add_window(
+            self.tgt0, (30.0, 50.0), merge_time=30.0, type="target", r_LP_P=np.zeros(3)
+        )
+        close_times = [opp["window"][1] for opp in sat.opportunities]
+        assert close_times == sorted(close_times)
+        # The merge still extends the original tgt0 window rather than duplicating it.
+        assert sat.opportunities_dict()[self.tgt0] == [(5.0, 50.0)]
+
     opportunities = [
         dict(object="downObj1", window=(10, 20), type="downlink"),
         dict(object="tgtObj1", window=(20, 30), type="target"),