diff --git a/src/bscPlugin/validation/ScopeValidator.spec.ts b/src/bscPlugin/validation/ScopeValidator.spec.ts
index 1cfdf536b..0007d5406 100644
--- a/src/bscPlugin/validation/ScopeValidator.spec.ts
+++ b/src/bscPlugin/validation/ScopeValidator.spec.ts
@@ -4900,6 +4900,79 @@ describe('ScopeValidator', () => {
             program.validate();
             expectZeroDiagnostics(program);
         });
+
+        it('detects when a union contains an incompatible type', () => {
+            program.setFile<BrsFile>('source/main.bs', `
+                function test(x as string or integer)
+                    print x + "world"
+                end function
+            `);
+            program.validate();
+            expectDiagnostics(program, [
+                DiagnosticMessages.operatorTypeMismatch('+', 'string or integer', 'string').message
+            ]);
+        });
+
+        it('allows comparing a void value against a dynamic value with =', () => {
+            program.setFile<BrsFile>('source/main.bs', `
+                sub logEvent(name as string)
+                    print name
+                end sub
+
+                sub main(input as dynamic)
+                    result = logEvent("started")
+                    if result = input
+                        print "same"
+                    else
+                        print "different"
+                    end if
+                end sub
+            `);
+            program.validate();
+            expectZeroDiagnostics(program);
+        });
+
+        it('allows comparing a void value against invalid with <>', () => {
+            program.setFile<BrsFile>('source/main.bs', `
+                sub getConfig()
+                end sub
+
+                sub main()
+                    config = getConfig()
+                    if config <> invalid
+                        print "config exists"
+                    else
+                        print "no config"
+                    end if
+                end sub
+            `);
+            program.validate();
+            expectZeroDiagnostics(program);
+        });
+
+        it('allows comparing a "void or <type>" union against invalid with <>', () => {
+            program.setFile<BrsFile>('source/main.bs', `
+                sub fetchChannelData()
+                end sub
+
+                sub main()
+                    channel = fetchChannelData()
+                    if true
+                        channel = {
+                            title: "Home"
+                        }
+                    end if
+
+                    if channel <> invalid
+                        print channel.title
+                    else
+                        print "no channel"
+                    end if
+                end sub
+            `);
+            program.validate();
+            expectZeroDiagnostics(program);
+        });
     });
 
     describe('memberAccessibilityMismatch', () => {
diff --git a/src/bscPlugin/validation/ScopeValidator.ts b/src/bscPlugin/validation/ScopeValidator.ts
index ee46f93d6..635029794 100644
--- a/src/bscPlugin/validation/ScopeValidator.ts
+++ b/src/bscPlugin/validation/ScopeValidator.ts
@@ -28,6 +28,7 @@ import type { XmlScope } from '../../XmlScope';
 import type { XmlFile } from '../../files/XmlFile';
 import { SGFieldTypes } from '../../parser/SGTypes';
 import { DynamicType } from '../../types/DynamicType';
+import { getAllTypesFromCompoundType } from '../../types/helpers';
 import { BscTypeKind } from '../../types/BscTypeKind';
 import type { BrsDocWithType } from '../../parser/BrightScriptDocParser';
 import brsDocParser from '../../parser/BrightScriptDocParser';
@@ -995,9 +996,23 @@ export class ScopeValidator {
             rightTypeToTest = rightType.underlyingType;
         }
 
-        if (isUnionType(leftType) || isUnionType(rightType)) {
-            // TODO: it is possible to validate based on innerTypes, but more complicated
-            // Because you need to verify each combination of types
+        if (isUnionType(leftTypeToTest) || isUnionType(rightTypeToTest)) {
+            // validate every combination of the union's inner types - if any combination is invalid,
+            // then it's possible for this operation to fail at runtime, so flag it
+            const leftTypesToTest = isUnionType(leftTypeToTest) ? getAllTypesFromCompoundType(leftTypeToTest) : [leftTypeToTest];
+            const rightTypesToTest = isUnionType(rightTypeToTest) ? getAllTypesFromCompoundType(rightTypeToTest) : [rightTypeToTest];
+
+            for (const leftInnerType of leftTypesToTest) {
+                for (const rightInnerType of rightTypesToTest) {
+                    if (!util.binaryOperatorResultType(leftInnerType, binaryExpr.tokens.operator, rightInnerType)) {
+                        this.addMultiScopeDiagnostic({
+                            ...DiagnosticMessages.operatorTypeMismatch(binaryExpr.tokens.operator.text, leftType.toString(), rightType.toString()),
+                            location: binaryExpr.location
+                        });
+                        return;
+                    }
+                }
+            }
             return;
         }
         const opResult = util.binaryOperatorResultType(leftTypeToTest, binaryExpr.tokens.operator, rightTypeToTest);
diff --git a/src/util.spec.ts b/src/util.spec.ts
index 774292c08..640d0ac98 100644
--- a/src/util.spec.ts
+++ b/src/util.spec.ts
@@ -12,7 +12,7 @@ import { NamespaceType } from './types/NamespaceType';
 import { ClassType } from './types/ClassType';
 import { ReferenceType } from './types/ReferenceType';
 import { SymbolTypeFlag } from './SymbolTypeFlag';
-import { BooleanType, DoubleType, DynamicType, FloatType, IntegerType, InterfaceType, InvalidType, LongIntegerType, ObjectType, StringType, TypedFunctionType, UnionType, VoidType } from './types';
+import { BooleanType, DoubleType, DynamicType, FloatType, IntegerType, InterfaceType, InvalidType, LongIntegerType, ObjectType, StringType, TypedFunctionType, UninitializedType, UnionType, VoidType } from './types';
 import { TokenKind } from './lexer/TokenKind';
 import { createToken } from './astUtils/creators';
 import { createDottedIdentifier, createVariableExpression } from './astUtils/creators';
@@ -1494,6 +1494,32 @@ describe('util', () => {
         it('handles object Types', () => {
             expectTypeToBe(util.binaryOperatorResultType(new ObjectType(), createToken(TokenKind.Plus), IntegerType.instance), IntegerType);
         });
+
+        it('allows = and <> comparisons of a void type against invalid', () => {
+            expectTypeToBe(util.binaryOperatorResultType(VoidType.instance, createToken(TokenKind.Equal), InvalidType.instance), BooleanType);
+            expectTypeToBe(util.binaryOperatorResultType(InvalidType.instance, createToken(TokenKind.Equal), VoidType.instance), BooleanType);
+            expectTypeToBe(util.binaryOperatorResultType(VoidType.instance, createToken(TokenKind.LessGreater), InvalidType.instance), BooleanType);
+            expectTypeToBe(util.binaryOperatorResultType(InvalidType.instance, createToken(TokenKind.LessGreater), VoidType.instance), BooleanType);
+        });
+
+        it('allows = and <> comparisons of a void type against dynamic', () => {
+            expectTypeToBe(util.binaryOperatorResultType(VoidType.instance, createToken(TokenKind.Equal), DynamicType.instance), BooleanType);
+            expectTypeToBe(util.binaryOperatorResultType(VoidType.instance, createToken(TokenKind.LessGreater), DynamicType.instance), BooleanType);
+        });
+
+        it('still disallows non-comparison operators on a void type', () => {
+            expect(util.binaryOperatorResultType(VoidType.instance, createToken(TokenKind.Plus), InvalidType.instance)).to.be.undefined;
+            expect(util.binaryOperatorResultType(VoidType.instance, createToken(TokenKind.Less), InvalidType.instance)).to.be.undefined;
+        });
+
+        it('still disallows comparisons of a void type against non-invalid/dynamic types', () => {
+            expect(util.binaryOperatorResultType(VoidType.instance, createToken(TokenKind.Equal), StringType.instance)).to.be.undefined;
+        });
+
+        it('still disallows = and <> comparisons of an uninitialized type against invalid', () => {
+            expect(util.binaryOperatorResultType(UninitializedType.instance, createToken(TokenKind.Equal), InvalidType.instance)).to.be.undefined;
+            expect(util.binaryOperatorResultType(UninitializedType.instance, createToken(TokenKind.LessGreater), InvalidType.instance)).to.be.undefined;
+        });
     });
 
     describe('unaryOperatorResultType', () => {
diff --git a/src/util.ts b/src/util.ts
index 2e7e48136..549b680be 100644
--- a/src/util.ts
+++ b/src/util.ts
@@ -1550,7 +1550,15 @@ export class Util {
             rightType = this.getHighestPriorityType(rightType.types);
         }
 
-        if (isVoidType(leftType) || isVoidType(rightType) || isUninitializedType(leftType) || isUninitializedType(rightType)) {
+        if (isUninitializedType(leftType) || isUninitializedType(rightType)) {
+            return undefined;
+        }
+        if (isVoidType(leftType) || isVoidType(rightType)) {
+            // = and <> can still be used to check a possibly-void value against invalid/dynamic
+            if ((operator.kind === TokenKind.Equal || operator.kind === TokenKind.LessGreater) &&
+                (isInvalidTypeLike(leftType) || isInvalidTypeLike(rightType) || isDynamicType(leftType) || isDynamicType(rightType))) {
+                return BooleanType.instance;
+            }
             return undefined;
         }