diff --git a/examples/data/pragmatic/basics/required-break.tricky.matrix.json b/examples/data/pragmatic/basics/required-break.tricky.matrix.json
new file mode 100644
index 000000000..b19fa68dd
--- /dev/null
+++ b/examples/data/pragmatic/basics/required-break.tricky.matrix.json
@@ -0,0 +1 @@
+{"profile": "normal_car", "durations": [0, 635, 24, 580, 27, 2232, 625, 0, 650, 76, 653, 2507, 24, 660, 0, 605, 3, 2257, 570, 95, 595, 0, 598, 2449, 27, 663, 3, 608, 0, 2260, 2232, 2545, 2257, 2515, 2260, 0], "distances": [0, 8888, 192, 8510, 215, 52931, 8896, 0, 9088, 450, 9111, 56579, 192, 9080, 0, 8702, 23, 53123, 8518, 450, 8710, 0, 8733, 60163, 215, 9103, 23, 8725, 0, 53146, 52996, 56684, 53188, 60477, 53211, 0]}
\ No newline at end of file
diff --git a/examples/data/pragmatic/basics/required-break.tricky.problem.json b/examples/data/pragmatic/basics/required-break.tricky.problem.json
new file mode 100644
index 000000000..77ab05952
--- /dev/null
+++ b/examples/data/pragmatic/basics/required-break.tricky.problem.json
@@ -0,0 +1,219 @@
+{
+  "plan": {
+    "jobs": [
+      {
+        "id": "0",
+        "pickups": null,
+        "deliveries": null,
+        "services": [
+          {
+            "places": [
+              {
+                "location": {
+                  "index": 0
+                },
+                "duration": 10800.0,
+                "times": [
+                  [
+                    "2026-01-19T00:00:00+11:00",
+                    "2026-01-19T23:59:59.999999+11:00"
+                  ]
+                ],
+                "tag": null
+              }
+            ]
+          }
+        ],
+        "replacements": null,
+        "skills": null
+      },
+      {
+        "id": "1",
+        "pickups": null,
+        "deliveries": null,
+        "services": [
+          {
+            "places": [
+              {
+                "location": {
+                  "index": 1
+                },
+                "duration": 3600.0,
+                "times": [
+                  [
+                    "2026-01-18T22:30:00+00:00",
+                    "2026-01-18T22:30:00+00:00"
+                  ]
+                ],
+                "tag": null
+              }
+            ]
+          }
+        ],
+        "replacements": null,
+        "skills": null
+      },
+      {
+        "id": "2",
+        "pickups": null,
+        "deliveries": null,
+        "services": [
+          {
+            "places": [
+              {
+                "location": {
+                  "index": 2
+                },
+                "duration": 1800.0,
+                "times": [
+                  [
+                    "2026-01-19T00:15:00+00:00",
+                    "2026-01-19T00:15:00+00:00"
+                  ]
+                ],
+                "tag": null
+              }
+            ]
+          }
+        ],
+        "replacements": null,
+        "skills": null
+      },
+      {
+        "id": "3",
+        "pickups": null,
+        "deliveries": null,
+        "services": [
+          {
+            "places": [
+              {
+                "location": {
+                  "index": 3
+                },
+                "duration": 5400.0,
+                "times": [
+                  [
+                    "2026-01-18T21:00:00+00:00",
+                    "2026-01-18T21:00:00+00:00"
+                  ]
+                ],
+                "tag": null
+              }
+            ]
+          }
+        ],
+        "replacements": null,
+        "skills": null
+      },
+      {
+        "id": "4",
+        "pickups": null,
+        "deliveries": null,
+        "services": [
+          {
+            "places": [
+              {
+                "location": {
+                  "index": 4
+                },
+                "duration": 1800.0,
+                "times": [
+                  [
+                    "2026-01-19T00:45:00+00:00",
+                    "2026-01-19T00:45:00+00:00"
+                  ]
+                ],
+                "tag": null
+              }
+            ]
+          }
+        ],
+        "replacements": null,
+        "skills": null
+      }
+    ],
+    "relations": [
+      {
+        "type": "sequence",
+        "jobs": [
+          "3",
+          "1",
+          "2",
+          "4"
+        ],
+        "vehicleId": "37",
+        "shiftIndex": 0
+      }
+    ]
+  },
+  "fleet": {
+    "vehicles": [
+      {
+        "typeId": "37",
+        "vehicleIds": [
+          "37"
+        ],
+        "profile": {
+          "matrix": "van"
+        },
+        "costs": {
+          "fixed": 22.0,
+          "distance": 0.0002,
+          "time": 0.004806
+        },
+        "shifts": [
+          {
+            "start": {
+              "earliest": "2026-01-19T08:00:00+11:00",
+              "location": {
+                "index": 5
+              },
+              "latest": "2026-01-19T08:00:00+11:00"
+            },
+            "end": {
+              "latest": "2026-01-19T16:00:00+11:00",
+              "location": {
+                "index": 5
+              },
+              "earliest": null
+            },
+            "breaks": [
+              {
+                "time": {
+                  "latest": 15303,
+                  "earliest": 15303
+                },
+                "duration": 1800
+              }
+            ],
+            "reloads": null
+          }
+        ],
+        "capacity": [
+          999
+        ],
+        "skills": []
+      }
+    ],
+    "profiles": [
+      {
+        "name": "van"
+      }
+    ]
+  },
+  "objectives": [
+    {
+      "type": "minimize-unassigned",
+      "breaks": 1.0
+    },
+    {
+      "type": "minimize-tours"
+    },
+    {
+      "type": "minimize-arrival-time"
+    },
+    {
+      "type": "minimize-cost"
+    }
+  ]
+}
diff --git a/examples/data/pragmatic/basics/required-break.tricky.solution.json b/examples/data/pragmatic/basics/required-break.tricky.solution.json
new file mode 100644
index 000000000..7dcf536c8
--- /dev/null
+++ b/examples/data/pragmatic/basics/required-break.tricky.solution.json
@@ -0,0 +1,168 @@
+{
+  "statistic": {
+    "cost": 133.735938,
+    "distance": 123184,
+    "duration": 18123,
+    "times": {
+      "driving": 5523,
+      "serving": 12600,
+      "waiting": 0,
+      "break": 0,
+      "commuting": 0,
+      "parking": 0
+    }
+  },
+  "tours": [
+    {
+      "vehicleId": "37",
+      "typeId": "37",
+      "shiftIndex": 0,
+      "stops": [
+        {
+          "location": {
+            "index": 5
+          },
+          "time": {
+            "arrival": "2026-01-18T21:00:00Z",
+            "departure": "2026-01-18T21:00:00Z"
+          },
+          "distance": 0,
+          "load": [
+            0
+          ],
+          "activities": [
+            {
+              "jobId": "departure",
+              "type": "departure"
+            }
+          ]
+        },
+        {
+          "location": {
+            "index": 3
+          },
+          "time": {
+            "arrival": "2026-01-18T21:41:55Z",
+            "departure": "2026-01-18T23:11:55Z"
+          },
+          "distance": 60477,
+          "load": [
+            0
+          ],
+          "activities": [
+            {
+              "jobId": "3",
+              "type": "service"
+            }
+          ]
+        },
+        {
+          "location": {
+            "index": 1
+          },
+          "time": {
+            "arrival": "2026-01-18T23:13:30Z",
+            "departure": "2026-01-19T00:13:30Z"
+          },
+          "distance": 60927,
+          "load": [
+            0
+          ],
+          "activities": [
+            {
+              "jobId": "1",
+              "type": "service"
+            }
+          ]
+        },
+        {
+          "location": {
+            "index": 2
+          },
+          "time": {
+            "arrival": "2026-01-19T00:24:20Z",
+            "departure": "2026-01-19T00:54:20Z"
+          },
+          "distance": 70015,
+          "load": [
+            0
+          ],
+          "activities": [
+            {
+              "jobId": "2",
+              "type": "service"
+            }
+          ]
+        },
+        {
+          "location": {
+            "index": 4
+          },
+          "time": {
+            "arrival": "2026-01-19T00:54:23Z",
+            "departure": "2026-01-19T01:24:23Z"
+          },
+          "distance": 70038,
+          "load": [
+            0
+          ],
+          "activities": [
+            {
+              "jobId": "4",
+              "type": "service"
+            }
+          ]
+        },
+        {
+          "location": {
+            "index": 5
+          },
+          "time": {
+            "arrival": "2026-01-19T02:02:03Z",
+            "departure": "2026-01-19T02:02:03Z"
+          },
+          "distance": 123184,
+          "load": [
+            0
+          ],
+          "activities": [
+            {
+              "jobId": "arrival",
+              "type": "arrival"
+            }
+          ]
+        }
+      ],
+      "statistic": {
+        "cost": 133.735938,
+        "distance": 123184,
+        "duration": 18123,
+        "times": {
+          "driving": 5523,
+          "serving": 12600,
+          "waiting": 0,
+          "break": 0,
+          "commuting": 0,
+          "parking": 0
+        }
+      }
+    }
+  ],
+  "unassigned": [
+    {
+      "jobId": "0",
+      "reasons": [
+        {
+          "code": "TIME_WINDOW_CONSTRAINT",
+          "description": "cannot be visited within time window",
+          "details": [
+            {
+              "vehicleId": "37",
+              "shiftIndex": 0
+            }
+          ]
+        }
+      ]
+    }
+  ]
+}
\ No newline at end of file
diff --git a/examples/json-pragmatic/src/main.rs b/examples/json-pragmatic/src/main.rs
index 490de7638..c168849a7 100644
--- a/examples/json-pragmatic/src/main.rs
+++ b/examples/json-pragmatic/src/main.rs
@@ -8,8 +8,8 @@ use std::sync::Arc;
 use vrp_pragmatic::checker::CheckerContext;
 use vrp_pragmatic::core::models::{Problem as CoreProblem, Solution as CoreSolution};
 use vrp_pragmatic::core::prelude::*;
-use vrp_pragmatic::format::problem::{Matrix, PragmaticProblem, Problem, deserialize_matrix, deserialize_problem};
-use vrp_pragmatic::format::solution::{Solution, deserialize_solution, write_pragmatic};
+use vrp_pragmatic::format::problem::{deserialize_matrix, deserialize_problem, Matrix, PragmaticProblem, Problem};
+use vrp_pragmatic::format::solution::{deserialize_solution, write_pragmatic, Solution};
 
 fn main() {
     let args: Vec<String> = std::env::args().collect();
@@ -29,6 +29,7 @@ fn run_examples(base_path: &str) {
         ("basics/priorities.value", None),
         ("basics/profiles.basic", Some(vec!["basics/profiles.basic.matrix.car", "basics/profiles.basic.matrix.truck"])),
         ("basics/relation-strict.basic", None),
+        ("basics/required-break.tricky", Some(vec!["basics/required-break.tricky.matrix"])),
         ("basics/relation-any.basic", None),
         ("basics/reload.basic", None),
         ("basics/reload.multi", None),