diff --git a/.eslintrc.js b/.eslintrc.js
index 016f619..bf39de4 100644
--- a/.eslintrc.js
+++ b/.eslintrc.js
@@ -6,6 +6,7 @@ module.exports = {
             plugins: ['jest'],
             extends: ['plugin:jest/all'],
             rules: {
+                'jest/expect-expect': ['error', { assertFunctionNames: ['expect*'] }],
                 'jest/prefer-expect-assertions': 'off',
                 'jest/prefer-lowercase-title': 'off',
                 'jest/max-expects': ['error', { max: 8 }],
diff --git a/src/__tests__/map.test.ts b/src/__tests__/map.test.ts
index cd99f7d..428b7f4 100644
--- a/src/__tests__/map.test.ts
+++ b/src/__tests__/map.test.ts
@@ -1,4 +1,6 @@
+import { Comparable } from '../comparable';
 import { DeepMap } from '../map';
+import { Options } from '../options';
 import { TestObjectField, TestObject } from './common/test.utils';
 
 describe('DeepMap', () => {
@@ -358,5 +360,67 @@ describe('DeepMap', () => {
                 expect([...differenceMap.entries()]).toStrictEqual([[new K('1'), new V('1')]]);
             });
         });
+
+        describe('Options checksum validation', () => {
+            type TestOptions = Options<number, number, number, number>;
+            type ComparableOperation = keyof Comparable<number>;
+
+            const operationTypes: ComparableOperation[] = ['equals', 'contains', 'union', 'intersection', 'difference'];
+            const errorMsg = 'Structures must use same options for Comparable interface operations';
+
+            const optionsA1: TestOptions = {};
+            const optionsA2: TestOptions = { useToJsonTransform: true };
+            const optionsA3: TestOptions = { transformer: (n) => n + 1 };
+            const optionsA4: TestOptions = { transformer: (k) => k + 1 };
+            const optionsA5: TestOptions = { transformer: (k) => k + 1, unorderedSets: true };
+            const optionsA6: TestOptions = { unorderedSets: true };
+            const optionsA7: TestOptions = undefined as unknown as TestOptions;
+
+            const optionsB1: TestOptions = {};
+            const optionsB2: TestOptions = { useToJsonTransform: true };
+            const optionsB3: TestOptions = { transformer: (n) => n + 1 };
+            const optionsB4: TestOptions = { transformer: (k) => k + 1 };
+            const optionsB5: TestOptions = { transformer: (k) => k + 1, unorderedSets: true };
+            const optionsB6: TestOptions = { unorderedSets: true };
+            const optionsB7: TestOptions = undefined as unknown as TestOptions;
+
+            function getMapWithOptions(options: TestOptions): DeepMap<number, number> {
+                return new DeepMap([[1, 1]], options);
+            }
+
+            function expectOptionsError(opts1: TestOptions, opts2: TestOptions, operation: ComparableOperation): void {
+                expect(() => getMapWithOptions(opts1)[operation](getMapWithOptions(opts2))).toThrow(errorMsg);
+            }
+
+            function expectNoOptionsError(
+                opts1: TestOptions,
+                opts2: TestOptions,
+                operation: ComparableOperation
+            ): void {
+                expect(() => getMapWithOptions(opts1)[operation](getMapWithOptions(opts2))).not.toThrow();
+            }
+
+            it.each(operationTypes)('error when attempting %s operation with different options', async (operation) => {
+                expectOptionsError(optionsA1, optionsA2, operation);
+                expectOptionsError(optionsA2, optionsA3, operation);
+                expectOptionsError(optionsA3, optionsA4, operation);
+                expectOptionsError(optionsA4, optionsA5, operation);
+                expectOptionsError(optionsA5, optionsA6, operation);
+                expectOptionsError(optionsA6, optionsA7, operation);
+            });
+
+            it.each(operationTypes)(
+                'no error when attempting %s operation with identical options',
+                async (operation) => {
+                    expectNoOptionsError(optionsA1, optionsB1, operation);
+                    expectNoOptionsError(optionsA2, optionsB2, operation);
+                    expectNoOptionsError(optionsA3, optionsB3, operation);
+                    expectNoOptionsError(optionsA4, optionsB4, operation);
+                    expectNoOptionsError(optionsA5, optionsB5, operation);
+                    expectNoOptionsError(optionsA6, optionsB6, operation);
+                    expectNoOptionsError(optionsA7, optionsB7, operation);
+                }
+            );
+        });
     });
 });
diff --git a/src/areEqual.ts b/src/areEqual.ts
index 81acbab..c63c1b0 100644
--- a/src/areEqual.ts
+++ b/src/areEqual.ts
@@ -1,3 +1,4 @@
+import { DeepEqualityDataStructuresError } from './errors';
 import { Options } from './options';
 import { DeepSet } from './set';
 
@@ -10,7 +11,7 @@ import { DeepSet } from './set';
  */
 export function areEqual<V, TxV = V>(values: V[], options?: Options<V, null, TxV, null>): boolean {
     if (values.length === 0) {
-        throw new Error('Empty values list passed to areEqual function');
+        throw new DeepEqualityDataStructuresError('Empty values list passed to areEqual function');
     }
     const set = new DeepSet(values, options);
     return set.size === 1;
diff --git a/src/errors.ts b/src/errors.ts
new file mode 100644
index 0000000..dff3b1c
--- /dev/null
+++ b/src/errors.ts
@@ -0,0 +1 @@
+export class DeepEqualityDataStructuresError extends Error {}
diff --git a/src/map.bi-directional.ts b/src/map.bi-directional.ts
index 44ec373..05159d3 100644
--- a/src/map.bi-directional.ts
+++ b/src/map.bi-directional.ts
@@ -1,3 +1,4 @@
+import { DeepEqualityDataStructuresError } from './errors';
 import { DeepMap } from './map';
 import { Normalized } from './normalizer';
 import { Options } from './options';
@@ -27,7 +28,7 @@ export class BiDirectionalDeepMap<K, V, TxK = K, TxV = V> extends DeepMap<K, V,
         // Enforce 1-to-1: Don't allow writing a value which is already present in the map for a different key
         const preexistingValueKey = this.getKeyByValue(val);
         if (preexistingValueKey !== undefined && this.normalizeKey(preexistingValueKey) !== this.normalizeKey(key)) {
-            throw new Error(
+            throw new DeepEqualityDataStructuresError(
                 `Could not set key='${stringify(key)}': The value='${stringify(
                     val
                 )}' is already associated with key='${stringify(preexistingValueKey)}'`
diff --git a/src/map.ts b/src/map.ts
index 3a4e450..246ed22 100644
--- a/src/map.ts
+++ b/src/map.ts
@@ -1,4 +1,5 @@
 import { Comparable } from './comparable';
+import { DeepEqualityDataStructuresError } from './errors';
 import { Normalized, Normalizer } from './normalizer';
 import { Options } from './options';
 
@@ -129,6 +130,7 @@ export class DeepMap<K, V, TxK = K, TxV = V> extends Map<K, V> implements Compar
      * @returns true if the entries of `other` are the same as this map
      */
     equals(other: this): boolean {
+        this.validateUsingSameOptionsAs(other);
         return this.size === other.size && this.contains(other);
     }
 
@@ -137,6 +139,7 @@ export class DeepMap<K, V, TxK = K, TxV = V> extends Map<K, V> implements Compar
      * @returns true if the entries of `other` are all contained in this map
      */
     contains(other: this): boolean {
+        this.validateUsingSameOptionsAs(other);
         return [...other.entries()].every(([key, val]) => this.keyValuePairIsPresentIn(key, val, this));
     }
 
@@ -147,6 +150,7 @@ export class DeepMap<K, V, TxK = K, TxV = V> extends Map<K, V> implements Compar
      * NOTE: If both maps prescribe the same key, the key-value pair from `this` will be retained.
      */
     union(other: this): DeepMap<K, V, TxK, TxV> {
+        this.validateUsingSameOptionsAs(other);
         return new DeepMap([...other.entries(), ...this.entries()], this.options);
     }
 
@@ -155,6 +159,8 @@ export class DeepMap<K, V, TxK = K, TxV = V> extends Map<K, V> implements Compar
      * @returns a new map containing all key-value pairs in `this` that are also present in `other`.
      */
     intersection(other: this): DeepMap<K, V, TxK, TxV> {
+        this.validateUsingSameOptionsAs(other);
+
         const intersectingPairs = [...this.entries()].filter(([key, val]) =>
             this.keyValuePairIsPresentIn(key, val, other)
         );
@@ -166,6 +172,8 @@ export class DeepMap<K, V, TxK = K, TxV = V> extends Map<K, V> implements Compar
      * @returns a new map containing all key-value pairs in `this` that are not present in `other`.
      */
     difference(other: this): DeepMap<K, V, TxK, TxV> {
+        this.validateUsingSameOptionsAs(other);
+
         const differencePairs = [...this.entries()].filter(
             ([key, val]) => !this.keyValuePairIsPresentIn(key, val, other)
         );
@@ -182,6 +190,14 @@ export class DeepMap<K, V, TxK = K, TxV = V> extends Map<K, V> implements Compar
         return this.normalizer.normalizeValue(input);
     }
 
+    private validateUsingSameOptionsAs(other: this): void {
+        if (this.normalizer.getOptionsChecksum() !== other['normalizer'].getOptionsChecksum()) {
+            throw new DeepEqualityDataStructuresError(
+                'Structures must use same options for Comparable interface operations'
+            );
+        }
+    }
+
     /**
      * @returns true if the key is present in the provided map w/ the specified value
      */
diff --git a/src/normalizer.ts b/src/normalizer.ts
index 8576d26..ba04d60 100644
--- a/src/normalizer.ts
+++ b/src/normalizer.ts
@@ -22,8 +22,11 @@ export class Normalizer<K, V, TxK, TxV> {
     private readonly caseInsensitive: boolean;
     private readonly keyTransformer: TransformFunction<K, TxK>;
     private readonly valueTransformer: TransformFunction<V, TxV>;
+    private readonly optionsChecksum: string;
 
     constructor(options: Options<K, V, TxK, TxV> = {}) {
+        this.optionsChecksum = hash(options);
+
         const { transformer, mapValueTransformer, useToJsonTransform, caseInsensitive, ...objectHashOptions } =
             getOptionsWithDefaults(options);
         this.objectHashOptions = objectHashOptions;
@@ -47,6 +50,13 @@ export class Normalizer<K, V, TxK, TxV> {
         }
     }
 
+    /**
+     * @returns the checksum for the options passed to this Normalizer
+     */
+    getOptionsChecksum(): string {
+        return this.optionsChecksum;
+    }
+
     /**
      * Normalize the input by transforming and then hashing the result (if an object)
      * @param input the input to normalize
diff --git a/src/set.ts b/src/set.ts
index f4f79b3..9f7aa4f 100644
--- a/src/set.ts
+++ b/src/set.ts
@@ -103,6 +103,7 @@ export class DeepSet<V, TxV = V> extends Set<V> implements Comparable<DeepSet<V,
     }
 
     /**
+     * @param other the set to compare against
      * @returns true if the values of `other` are the same as this set
      */
     equals(other: this): boolean {
@@ -110,6 +111,7 @@ export class DeepSet<V, TxV = V> extends Set<V> implements Comparable<DeepSet<V,
     }
 
     /**
+     * @param other the set to compare against
      * @returns true if the values of `other` are all contained in this set
      */
     contains(other: this): boolean {
@@ -117,15 +119,15 @@ export class DeepSet<V, TxV = V> extends Set<V> implements Comparable<DeepSet<V,
     }
 
     /**
+     * @param other the set to compare against
      * @returns a new set whose values are the union of `this` and `other`.
-     *
-     * NOTE: If both maps prescribe the same key, the value from `other` will be retained.
      */
     union(other: this): DeepSet<V, TxV> {
         return this.getSetFromMapKeys(this.map.union(other['map']));
     }
 
     /**
+     * @param other the set to compare against
      * @returns a new set containing all values in `this` that are also in `other`.
      */
     intersection(other: this): DeepSet<V, TxV> {
@@ -133,6 +135,7 @@ export class DeepSet<V, TxV = V> extends Set<V> implements Comparable<DeepSet<V,
     }
 
     /**
+     * @param other the set to compare against
      * @returns a new set containing all values in `this` that are not also in `other`.
      */
     difference(other: this): DeepSet<V, TxV> {