diff --git a/CHANGELOG.md b/CHANGELOG.md
index 1b420144ba1..29c7005a3b7 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -24,6 +24,8 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - Removed a spurious error message "'torch.cuda' has no attribute '_check_driver'" that would be appear in the logs
   when a `ConfigurationError` for missing GPU was raised.
 - Load model on CPU post training to save GPU memory.
+- Fixed a bug in `ShouldValidateCallback` that leads to valuation occuring after the first epoch regardless of `validation_start` value.
+- Fixed a bug in `ShouldValidateCallback` that leads to valuation occuring every `validation_interval + 1` epochs, instead of every `validation_interval` epochs.
 
 ### Removed
 
diff --git a/allennlp/training/callbacks/should_validate.py b/allennlp/training/callbacks/should_validate.py
index a1008fc70a6..9ed801523d1 100644
--- a/allennlp/training/callbacks/should_validate.py
+++ b/allennlp/training/callbacks/should_validate.py
@@ -25,6 +25,11 @@ def __init__(
         self._validation_start = validation_start
         self._validation_interval = validation_interval
 
+    def on_start(
+        self, trainer: "GradientDescentTrainer", is_primary: bool = True, **kwargs
+    ) -> None:
+        trainer._should_validate_this_epoch = self._should_validate(epoch=0)
+
     def on_epoch(
         self,
         trainer: "GradientDescentTrainer",
@@ -33,9 +38,12 @@ def on_epoch(
         is_primary: bool = True,
         **kwargs,
     ) -> None:
+        trainer._should_validate_this_epoch = self._should_validate(epoch=epoch + 1)
+
+    def _should_validate(self, epoch: int) -> bool:
+        should_validate = True
         if self._validation_start is not None and epoch < self._validation_start:
-            trainer._should_validate_this_epoch = False
+            should_validate = False
         elif self._validation_interval is not None and epoch % self._validation_interval != 0:
-            trainer._should_validate_this_epoch = False
-        else:
-            trainer._should_validate_this_epoch = True
+            should_validate = False
+        return should_validate
diff --git a/tests/training/trainer_test.py b/tests/training/trainer_test.py
index 576a61d2183..bad84580000 100644
--- a/tests/training/trainer_test.py
+++ b/tests/training/trainer_test.py
@@ -1361,16 +1361,20 @@ def test_should_validate_callback(self):
         )
         trainer.train()
 
-        # Doesn't satisfy 'validation_start' or 'validation_interval'
+        # Shouldn't validate on the first epoch as it's before the 'validation_start'
+        callback.on_start(trainer)
+        assert not trainer._should_validate_this_epoch
+
+        # Satisfies 'validation_interval' but not 'validation_start'
         callback.on_epoch(trainer, metrics={}, epoch=1)
         assert not trainer._should_validate_this_epoch
 
-        # Satisfies 'validation_start' but not 'validation_interval'
+        # Doesn't satisfy 'validation_start' or 'validation_interval'
         callback.on_epoch(trainer, metrics={}, epoch=2)
         assert not trainer._should_validate_this_epoch
 
         # Satisfies both 'validation_start' and 'validation_interval'
-        callback.on_epoch(trainer, metrics={}, epoch=4)
+        callback.on_epoch(trainer, metrics={}, epoch=5)
         assert trainer._should_validate_this_epoch