diff --git a/scripts/startup/bl_ui/properties_constraint.py b/scripts/startup/bl_ui/properties_constraint.py
index 66f2195d348..1a01714b525 100644
--- a/scripts/startup/bl_ui/properties_constraint.py
+++ b/scripts/startup/bl_ui/properties_constraint.py
@@ -233,6 +233,7 @@ class ConstraintButtonsPanel:
 
         layout.prop(con, "euler_order", text="Order")
         layout.prop(con, "use_transform_limit")
+        layout.prop(con, "use_legacy_behavior")
         self.space_template(layout, con, target=False, owner=True)
 
         self.draw_influence(layout, con)
diff --git a/source/blender/blenkernel/BKE_blender_version.h b/source/blender/blenkernel/BKE_blender_version.h
index 30c6f3f823f..678124d8a87 100644
--- a/source/blender/blenkernel/BKE_blender_version.h
+++ b/source/blender/blenkernel/BKE_blender_version.h
@@ -29,7 +29,7 @@ extern "C" {
 
 /* Blender file format version. */
 #define BLENDER_FILE_VERSION BLENDER_VERSION
-#define BLENDER_FILE_SUBVERSION 59
+#define BLENDER_FILE_SUBVERSION 60
 
 /* Minimum Blender version that supports reading file written with the current
  * version. Older Blender versions will test this and cancel loading the file, showing a warning to
diff --git a/source/blender/blenkernel/intern/constraint.cc b/source/blender/blenkernel/intern/constraint.cc
index 7e575b5111c..a5a8cfa5ade 100644
--- a/source/blender/blenkernel/intern/constraint.cc
+++ b/source/blender/blenkernel/intern/constraint.cc
@@ -1758,17 +1758,43 @@ static void rotlimit_evaluate(bConstraint *con, bConstraintOb *cob, ListBase * /
 
   mat4_to_eulO(eul, rot_order, cob->matrix);
 
-  /* constraint data uses radians internally */
-
-  /* limiting of euler values... */
-  if (data->flag & LIMIT_XROT) {
-    eul[0] = clamp_angle(eul[0], data->xmin, data->xmax);
+  /* Limit the euler values. */
+  if (data->flag & LIMIT_ROT_LEGACY_BEHAVIOR) {
+    /* The legacy behavior, which just does a naive clamping of the angles as
+     * simple numbers. Since the input angles are always in the range [-180,
+     * 180] degrees due to being derived from matrix decomposition, this naive
+     * approach causes problems when rotations cross 180 degrees. Specifically,
+     * it results in unpredictable and unwanted rotation flips of the
+     * constrained objects/bones, especially when the constraint isn't in local
+     * space.
+     *
+     * The correct thing to do is a more sophisticated form of clamping that
+     * treats the angles as existing on a continuous loop, which is what the
+     * non-legacy behavior further below does. However, for backwards
+     * compatibility we are preserving this old behavior behind an option.
+     *
+     * See issues #117927 and #123105 for additional background. */
+    if (data->flag & LIMIT_XROT) {
+      eul[0] = clamp_f(eul[0], data->xmin, data->xmax);
+    }
+    if (data->flag & LIMIT_YROT) {
+      eul[1] = clamp_f(eul[1], data->ymin, data->ymax);
+    }
+    if (data->flag & LIMIT_ZROT) {
+      eul[2] = clamp_f(eul[2], data->zmin, data->zmax);
+    }
   }
-  if (data->flag & LIMIT_YROT) {
-    eul[1] = clamp_angle(eul[1], data->ymin, data->ymax);
-  }
-  if (data->flag & LIMIT_ZROT) {
-    eul[2] = clamp_angle(eul[2], data->zmin, data->zmax);
+  else {
+    /* The correct, non-legacy behavior. */
+    if (data->flag & LIMIT_XROT) {
+      eul[0] = clamp_angle(eul[0], data->xmin, data->xmax);
+    }
+    if (data->flag & LIMIT_YROT) {
+      eul[1] = clamp_angle(eul[1], data->ymin, data->ymax);
+    }
+    if (data->flag & LIMIT_ZROT) {
+      eul[2] = clamp_angle(eul[2], data->zmin, data->zmax);
+    }
   }
 
   loc_eulO_size_to_mat4(cob->matrix, loc, eul, size, rot_order);
diff --git a/source/blender/blenloader/intern/versioning_400.cc b/source/blender/blenloader/intern/versioning_400.cc
index 5b1a89aee52..478f376d073 100644
--- a/source/blender/blenloader/intern/versioning_400.cc
+++ b/source/blender/blenloader/intern/versioning_400.cc
@@ -17,6 +17,7 @@
 #include "DNA_anim_types.h"
 #include "DNA_brush_types.h"
 #include "DNA_camera_types.h"
+#include "DNA_constraint_types.h"
 #include "DNA_curve_types.h"
 #include "DNA_defaults.h"
 #include "DNA_light_types.h"
@@ -4165,6 +4166,31 @@ void blo_do_versions_400(FileData *fd, Library * /*lib*/, Main *bmain)
     FOREACH_NODETREE_END;
   }
 
+  if (!MAIN_VERSION_FILE_ATLEAST(bmain, 402, 60)) {
+    /* Limit Rotation constraints from old files should use the legacy Limit
+     * Rotation behavior. */
+    LISTBASE_FOREACH (Object *, obj, &bmain->objects) {
+      LISTBASE_FOREACH (bConstraint *, constraint, &obj->constraints) {
+        if (constraint->type != CONSTRAINT_TYPE_ROTLIMIT) {
+          continue;
+        }
+        static_cast<bRotLimitConstraint *>(constraint->data)->flag |= LIMIT_ROT_LEGACY_BEHAVIOR;
+      }
+
+      if (!obj->pose) {
+        continue;
+      }
+      LISTBASE_FOREACH (bPoseChannel *, pbone, &obj->pose->chanbase) {
+        LISTBASE_FOREACH (bConstraint *, constraint, &pbone->constraints) {
+          if (constraint->type != CONSTRAINT_TYPE_ROTLIMIT) {
+            continue;
+          }
+          static_cast<bRotLimitConstraint *>(constraint->data)->flag |= LIMIT_ROT_LEGACY_BEHAVIOR;
+        }
+      }
+    }
+  }
+
   /**
    * Always bump subversion in BKE_blender_version.h when adding versioning
    * code here, and wrap it inside a MAIN_VERSION_FILE_ATLEAST check.
diff --git a/source/blender/makesdna/DNA_constraint_types.h b/source/blender/makesdna/DNA_constraint_types.h
index 5a36d2f0b66..e4b0e94b408 100644
--- a/source/blender/makesdna/DNA_constraint_types.h
+++ b/source/blender/makesdna/DNA_constraint_types.h
@@ -1067,6 +1067,11 @@ typedef enum eRotLimit_Flags {
   LIMIT_XROT = (1 << 0),
   LIMIT_YROT = (1 << 1),
   LIMIT_ZROT = (1 << 2),
+
+  /* Use the legacy behavior of the Limit Rotation constraint. See the
+   * implementation of `rotlimit_evaluate()` in constraint.cc for more
+   * details. */
+  LIMIT_ROT_LEGACY_BEHAVIOR = (1 << 3),
 } eRotLimit_Flags;
 
 /* distance limit constraint */
diff --git a/source/blender/makesrna/intern/rna_constraint.cc b/source/blender/makesrna/intern/rna_constraint.cc
index 18b54ef216a..45eb79e5c30 100644
--- a/source/blender/makesrna/intern/rna_constraint.cc
+++ b/source/blender/makesrna/intern/rna_constraint.cc
@@ -2690,6 +2690,14 @@ static void rna_def_constraint_rotation_limit(BlenderRNA *brna)
       prop, "Affect Transform", "Transform tools are affected by this constraint as well");
   RNA_def_property_update(prop, NC_OBJECT | ND_CONSTRAINT, "rna_Constraint_update");
 
+  prop = RNA_def_property(srna, "use_legacy_behavior", PROP_BOOLEAN, PROP_NONE);
+  RNA_def_property_boolean_sdna(prop, nullptr, "flag", LIMIT_ROT_LEGACY_BEHAVIOR);
+  RNA_def_property_ui_text(
+      prop,
+      "Legacy Behavior",
+      "Use the old semi-broken behavior that doesn't understand that rotations loop around");
+  RNA_def_property_update(prop, NC_OBJECT | ND_CONSTRAINT, "rna_Constraint_update");
+
   RNA_define_lib_overridable(false);
 }