diff --git a/spark/v3.3/spark-extensions/src/test/java/org/apache/iceberg/spark/extensions/TestRollbackToTimestampProcedure.java b/spark/v3.3/spark-extensions/src/test/java/org/apache/iceberg/spark/extensions/TestRollbackToTimestampProcedure.java
index 281bfbf7ad1b..c65be60cc1a7 100644
--- a/spark/v3.3/spark-extensions/src/test/java/org/apache/iceberg/spark/extensions/TestRollbackToTimestampProcedure.java
+++ b/spark/v3.3/spark-extensions/src/test/java/org/apache/iceberg/spark/extensions/TestRollbackToTimestampProcedure.java
@@ -20,6 +20,8 @@
 
 import static org.assertj.core.api.Assertions.assertThatThrownBy;
 
+import java.sql.Timestamp;
+import java.time.Instant;
 import java.time.LocalDateTime;
 import java.util.List;
 import java.util.Map;
@@ -252,6 +254,39 @@ public void testRollbackToTimestampWithoutExplicitCatalog() {
         sql("SELECT * FROM %s ORDER BY id", tableName));
   }
 
+  @Test
+  public void testRollbackToTimestampBeforeOrEqualToOldestSnapshot() {
+    sql("CREATE TABLE %s (id bigint NOT NULL, data string) USING iceberg", tableName);
+    sql("INSERT INTO TABLE %s VALUES (1, 'a')", tableName);
+
+    Table table = validationCatalog.loadTable(tableIdent);
+    Snapshot firstSnapshot = table.currentSnapshot();
+    Timestamp beforeFirstSnapshot =
+        Timestamp.from(Instant.ofEpochMilli(firstSnapshot.timestampMillis() - 1));
+    Timestamp exactFirstSnapshot =
+        Timestamp.from(Instant.ofEpochMilli(firstSnapshot.timestampMillis()));
+
+    assertThatThrownBy(
+            () ->
+                sql(
+                    "CALL %s.system.rollback_to_timestamp(timestamp => TIMESTAMP '%s', table => '%s')",
+                    catalogName, beforeFirstSnapshot, tableIdent))
+        .isInstanceOf(IllegalArgumentException.class)
+        .hasMessage(
+            "Cannot roll back, no valid snapshot older than: %s",
+            beforeFirstSnapshot.toInstant().toEpochMilli());
+
+    assertThatThrownBy(
+            () ->
+                sql(
+                    "CALL %s.system.rollback_to_timestamp(timestamp => TIMESTAMP '%s', table => '%s')",
+                    catalogName, exactFirstSnapshot, tableIdent))
+        .isInstanceOf(IllegalArgumentException.class)
+        .hasMessage(
+            "Cannot roll back, no valid snapshot older than: %s",
+            exactFirstSnapshot.toInstant().toEpochMilli());
+  }
+
   @Test
   public void testInvalidRollbackToTimestampCases() {
     String timestamp = "TIMESTAMP '2007-12-03T10:15:30'";
diff --git a/spark/v3.4/spark-extensions/src/test/java/org/apache/iceberg/spark/extensions/TestRollbackToTimestampProcedure.java b/spark/v3.4/spark-extensions/src/test/java/org/apache/iceberg/spark/extensions/TestRollbackToTimestampProcedure.java
index 82df7567fce6..1cfe1ecf83be 100644
--- a/spark/v3.4/spark-extensions/src/test/java/org/apache/iceberg/spark/extensions/TestRollbackToTimestampProcedure.java
+++ b/spark/v3.4/spark-extensions/src/test/java/org/apache/iceberg/spark/extensions/TestRollbackToTimestampProcedure.java
@@ -20,6 +20,8 @@
 
 import static org.assertj.core.api.Assertions.assertThatThrownBy;
 
+import java.sql.Timestamp;
+import java.time.Instant;
 import java.time.LocalDateTime;
 import java.util.List;
 import java.util.Map;
@@ -252,6 +254,39 @@ public void testRollbackToTimestampWithoutExplicitCatalog() {
         sql("SELECT * FROM %s ORDER BY id", tableName));
   }
 
+  @Test
+  public void testRollbackToTimestampBeforeOrEqualToOldestSnapshot() {
+    sql("CREATE TABLE %s (id bigint NOT NULL, data string) USING iceberg", tableName);
+    sql("INSERT INTO TABLE %s VALUES (1, 'a')", tableName);
+
+    Table table = validationCatalog.loadTable(tableIdent);
+    Snapshot firstSnapshot = table.currentSnapshot();
+    Timestamp beforeFirstSnapshot =
+        Timestamp.from(Instant.ofEpochMilli(firstSnapshot.timestampMillis() - 1));
+    Timestamp exactFirstSnapshot =
+        Timestamp.from(Instant.ofEpochMilli(firstSnapshot.timestampMillis()));
+
+    assertThatThrownBy(
+            () ->
+                sql(
+                    "CALL %s.system.rollback_to_timestamp(timestamp => TIMESTAMP '%s', table => '%s')",
+                    catalogName, beforeFirstSnapshot, tableIdent))
+        .isInstanceOf(IllegalArgumentException.class)
+        .hasMessage(
+            "Cannot roll back, no valid snapshot older than: %s",
+            beforeFirstSnapshot.toInstant().toEpochMilli());
+
+    assertThatThrownBy(
+            () ->
+                sql(
+                    "CALL %s.system.rollback_to_timestamp(timestamp => TIMESTAMP '%s', table => '%s')",
+                    catalogName, exactFirstSnapshot, tableIdent))
+        .isInstanceOf(IllegalArgumentException.class)
+        .hasMessage(
+            "Cannot roll back, no valid snapshot older than: %s",
+            exactFirstSnapshot.toInstant().toEpochMilli());
+  }
+
   @Test
   public void testInvalidRollbackToTimestampCases() {
     String timestamp = "TIMESTAMP '2007-12-03T10:15:30'";
diff --git a/spark/v3.5/spark-extensions/src/test/java/org/apache/iceberg/spark/extensions/TestRollbackToTimestampProcedure.java b/spark/v3.5/spark-extensions/src/test/java/org/apache/iceberg/spark/extensions/TestRollbackToTimestampProcedure.java
index 08e6b1323c79..6b74391898e0 100644
--- a/spark/v3.5/spark-extensions/src/test/java/org/apache/iceberg/spark/extensions/TestRollbackToTimestampProcedure.java
+++ b/spark/v3.5/spark-extensions/src/test/java/org/apache/iceberg/spark/extensions/TestRollbackToTimestampProcedure.java
@@ -21,6 +21,8 @@
 import static org.assertj.core.api.Assertions.assertThatThrownBy;
 import static org.assertj.core.api.Assumptions.assumeThat;
 
+import java.sql.Timestamp;
+import java.time.Instant;
 import java.time.LocalDateTime;
 import java.util.List;
 import org.apache.iceberg.Snapshot;
@@ -246,6 +248,39 @@ public void testRollbackToTimestampWithoutExplicitCatalog() {
         sql("SELECT * FROM %s ORDER BY id", tableName));
   }
 
+  @TestTemplate
+  public void testRollbackToTimestampBeforeOrEqualToOldestSnapshot() {
+    sql("CREATE TABLE %s (id bigint NOT NULL, data string) USING iceberg", tableName);
+    sql("INSERT INTO TABLE %s VALUES (1, 'a')", tableName);
+
+    Table table = validationCatalog.loadTable(tableIdent);
+    Snapshot firstSnapshot = table.currentSnapshot();
+    Timestamp beforeFirstSnapshot =
+        Timestamp.from(Instant.ofEpochMilli(firstSnapshot.timestampMillis() - 1));
+    Timestamp exactFirstSnapshot =
+        Timestamp.from(Instant.ofEpochMilli(firstSnapshot.timestampMillis()));
+
+    assertThatThrownBy(
+            () ->
+                sql(
+                    "CALL %s.system.rollback_to_timestamp(timestamp => TIMESTAMP '%s', table => '%s')",
+                    catalogName, beforeFirstSnapshot, tableIdent))
+        .isInstanceOf(IllegalArgumentException.class)
+        .hasMessage(
+            "Cannot roll back, no valid snapshot older than: %s",
+            beforeFirstSnapshot.toInstant().toEpochMilli());
+
+    assertThatThrownBy(
+            () ->
+                sql(
+                    "CALL %s.system.rollback_to_timestamp(timestamp => TIMESTAMP '%s', table => '%s')",
+                    catalogName, exactFirstSnapshot, tableIdent))
+        .isInstanceOf(IllegalArgumentException.class)
+        .hasMessage(
+            "Cannot roll back, no valid snapshot older than: %s",
+            exactFirstSnapshot.toInstant().toEpochMilli());
+  }
+
   @TestTemplate
   public void testInvalidRollbackToTimestampCases() {
     String timestamp = "TIMESTAMP '2007-12-03T10:15:30'";