diff --git a/wpilibc/src/main/native/cpp/trajectory/TrajectoryParameterizer.cpp b/wpilibc/src/main/native/cpp/trajectory/TrajectoryParameterizer.cpp
index 131ae8a421..976b4e26e6 100644
--- a/wpilibc/src/main/native/cpp/trajectory/TrajectoryParameterizer.cpp
+++ b/wpilibc/src/main/native/cpp/trajectory/TrajectoryParameterizer.cpp
@@ -1,5 +1,5 @@
 /*----------------------------------------------------------------------------*/
-/* Copyright (c) 2019 FIRST. All Rights Reserved.                             */
+/* Copyright (c) 2019-2020 FIRST. All Rights Reserved.                        */
 /* Open Source Software - may be modified and shared by FRC teams. The code   */
 /* must be accompanied by the FIRST BSD license file in the root directory of */
 /* the project.                                                               */
@@ -31,6 +31,8 @@
 
 #include "frc/trajectory/TrajectoryParameterizer.h"
 
+#include <string>
+
 using namespace frc;
 
 Trajectory TrajectoryParameterizer::TimeParameterizeTrajectory(
@@ -186,8 +188,9 @@ Trajectory TrajectoryParameterizer::TimeParameterizeTrajectory(
         // delta_x = v * t
         dt = ds / v;
       } else {
-        throw std::runtime_error(
-            "Something went wrong during trajectory generation.");
+        throw std::runtime_error("Something went wrong at iteration " +
+                                 std::to_string(i) +
+                                 " of time parameterization.");
       }
     }
 
@@ -213,6 +216,14 @@ void TrajectoryParameterizer::EnforceAccelerationLimits(
     auto minMaxAccel = constraint->MinMaxAcceleration(
         state->pose.first, state->pose.second, state->maxVelocity * factor);
 
+    if (minMaxAccel.minAcceleration > minMaxAccel.maxAcceleration) {
+      throw std::runtime_error(
+          "The constraint's min acceleration was greater than its max "
+          "acceleration. To debug this, remove all constraints from the config "
+          "and add each one individually. If the offending constraint was "
+          "packaged with WPILib, please file a bug report.");
+    }
+
     state->minAcceleration = units::math::max(
         state->minAcceleration,
         reverse ? -minMaxAccel.maxAcceleration : minMaxAccel.minAcceleration);
diff --git a/wpilibj/src/main/java/edu/wpi/first/wpilibj/trajectory/TrajectoryParameterizer.java b/wpilibj/src/main/java/edu/wpi/first/wpilibj/trajectory/TrajectoryParameterizer.java
index 9459dd0cd0..e2bda033fa 100644
--- a/wpilibj/src/main/java/edu/wpi/first/wpilibj/trajectory/TrajectoryParameterizer.java
+++ b/wpilibj/src/main/java/edu/wpi/first/wpilibj/trajectory/TrajectoryParameterizer.java
@@ -1,5 +1,5 @@
 /*----------------------------------------------------------------------------*/
-/* Copyright (c) 2019 FIRST. All Rights Reserved.                             */
+/* Copyright (c) 2019-2020 FIRST. All Rights Reserved.                        */
 /* Open Source Software - may be modified and shared by FRC teams. The code   */
 /* must be accompanied by the FIRST BSD license file in the root directory of */
 /* the project.                                                               */
@@ -69,8 +69,7 @@ public final class TrajectoryParameterizer {
    * @return The trajectory.
    */
   @SuppressWarnings({"PMD.ExcessiveMethodLength", "PMD.CyclomaticComplexity",
-      "PMD.NPathComplexity", "PMD.AvoidInstantiatingObjectsInLoops",
-      "PMD.AvoidThrowingRawExceptionTypes"})
+      "PMD.NPathComplexity", "PMD.AvoidInstantiatingObjectsInLoops"})
   public static Trajectory timeParameterizeTrajectory(
       List<PoseWithCurvature> points,
       List<TrajectoryConstraint> constraints,
@@ -236,7 +235,8 @@ public final class TrajectoryParameterizer {
           // delta_x = v * t
           dt = ds / velocityMetersPerSecond;
         } else {
-          throw new RuntimeException("Something went wrong");
+          throw new TrajectoryGenerationException("Something went wrong at iteration " + i
+              + " of time parameterization.");
         }
       }
 
@@ -266,6 +266,14 @@ public final class TrajectoryParameterizer {
           state.pose.poseMeters, state.pose.curvatureRadPerMeter,
           state.maxVelocityMetersPerSecond * factor);
 
+      if (minMaxAccel.minAccelerationMetersPerSecondSq
+          > minMaxAccel.maxAccelerationMetersPerSecondSq) {
+        throw new TrajectoryGenerationException("The constraint's min acceleration "
+            + "was greater than its max acceleration.\n Offending Constraint: "
+            + constraint.getClass().getName()
+            + "\n If the offending constraint was packaged with WPILib, please file a bug report.");
+      }
+
       state.minAccelerationMetersPerSecondSq = Math.max(state.minAccelerationMetersPerSecondSq,
           reverse ? -minMaxAccel.maxAccelerationMetersPerSecondSq
               : minMaxAccel.minAccelerationMetersPerSecondSq);
@@ -300,4 +308,10 @@ public final class TrajectoryParameterizer {
       pose = new PoseWithCurvature();
     }
   }
+
+  public static class TrajectoryGenerationException extends RuntimeException {
+    public TrajectoryGenerationException(String message) {
+      super(message);
+    }
+  }
 }