diff --git a/.global.editorconfig.ini b/.global.editorconfig.ini
index db8ef801fc..3a8906f759 100644
--- a/.global.editorconfig.ini
+++ b/.global.editorconfig.ini
@@ -43,6 +43,9 @@ dotnet_diagnostic.BHI1200.severity = error
 # Inferred type of branches of ternary expression in interpolation don't match
 dotnet_diagnostic.BHI1210.severity = error
 
+# Declare checked operators
+dotnet_diagnostic.BHI1300.severity = warning
+
 # Call to FirstOrDefault when elements are of a value type; FirstOrNull may have been intended
 dotnet_diagnostic.BHI3100.severity = error
 # Use .Order()/.OrderDescending() shorthand
diff --git a/ExternalProjects/AnalyzersCommon/RoslynUtils.cs b/ExternalProjects/AnalyzersCommon/RoslynUtils.cs
index 8710e0be71..43e9c33831 100644
--- a/ExternalProjects/AnalyzersCommon/RoslynUtils.cs
+++ b/ExternalProjects/AnalyzersCommon/RoslynUtils.cs
@@ -1,5 +1,7 @@
 namespace BizHawk.Analyzers;
 
+using System.Collections.Generic;
+using System.Linq;
 using System.Threading;
 
 public static class RoslynUtils
@@ -11,6 +13,63 @@ public static class RoslynUtils
 		return parent;
 	}
 
+	public static string GetMethodName(this ConversionOperatorDeclarationSyntax cods)
+		=> cods.ImplicitOrExplicitKeyword.ToString() is "implicit"
+			? WellKnownMemberNames.ImplicitConversionName
+			: cods.CheckedKeyword.IsEmpty()
+				? WellKnownMemberNames.ExplicitConversionName
+				: WellKnownMemberNames.CheckedExplicitConversionName;
+
+	public static string GetMethodName(this OperatorDeclarationSyntax ods)
+		=> ods.OperatorToken.ToString() switch
+		{
+			"!" => WellKnownMemberNames.LogicalNotOperatorName,
+			"!=" => WellKnownMemberNames.InequalityOperatorName,
+			"%" => WellKnownMemberNames.ModulusOperatorName,
+			"&" => WellKnownMemberNames.BitwiseAndOperatorName,
+			"&&" => WellKnownMemberNames.LogicalAndOperatorName,
+			"*" => ods.CheckedKeyword.IsEmpty()
+				? WellKnownMemberNames.MultiplyOperatorName
+				: WellKnownMemberNames.CheckedMultiplyOperatorName,
+			"+" => ods.ParameterList.Parameters.Count is 1
+				? WellKnownMemberNames.UnaryPlusOperatorName
+				: ods.CheckedKeyword.IsEmpty()
+					? WellKnownMemberNames.AdditionOperatorName
+					: WellKnownMemberNames.CheckedAdditionOperatorName,
+			"++" => ods.CheckedKeyword.IsEmpty()
+				? WellKnownMemberNames.IncrementOperatorName
+				: WellKnownMemberNames.CheckedIncrementOperatorName,
+			"-" => ods.ParameterList.Parameters.Count is 1
+				? ods.CheckedKeyword.IsEmpty()
+					? WellKnownMemberNames.UnaryNegationOperatorName
+					: WellKnownMemberNames.CheckedUnaryNegationOperatorName
+				: ods.CheckedKeyword.IsEmpty()
+					? WellKnownMemberNames.SubtractionOperatorName
+					: WellKnownMemberNames.CheckedSubtractionOperatorName,
+			"--" => ods.CheckedKeyword.IsEmpty()
+				? WellKnownMemberNames.DecrementOperatorName
+				: WellKnownMemberNames.CheckedDecrementOperatorName,
+			"/" => ods.CheckedKeyword.IsEmpty()
+				? WellKnownMemberNames.DivisionOperatorName
+				: WellKnownMemberNames.CheckedDivisionOperatorName,
+			"<" => WellKnownMemberNames.LessThanOperatorName,
+			"<<" => WellKnownMemberNames.LeftShiftOperatorName,
+			"<=" => WellKnownMemberNames.LessThanOrEqualOperatorName,
+			"==" => WellKnownMemberNames.EqualityOperatorName,
+			">" => WellKnownMemberNames.GreaterThanOperatorName,
+			">=" => WellKnownMemberNames.GreaterThanOrEqualOperatorName,
+			">>" => WellKnownMemberNames.RightShiftOperatorName,
+			">>>" => WellKnownMemberNames.UnsignedRightShiftOperatorName,
+			"^" => WellKnownMemberNames.ExclusiveOrOperatorName,
+			"false" => WellKnownMemberNames.FalseOperatorName,
+			"true" => WellKnownMemberNames.TrueOperatorName,
+			"|" => WellKnownMemberNames.BitwiseOrOperatorName,
+			"||" => WellKnownMemberNames.LogicalOrOperatorName,
+			"~" => WellKnownMemberNames.OnesComplementOperatorName,
+			// ...and some operators only exist in VB.NET (dw, you're not missing anything)
+			_ => throw new ArgumentException(paramName: nameof(ods), message: "pretend this is a BHI6660 unexpected token in AST (in this case, a new kind of operator was added to C#)")
+		};
+
 	private static ITypeSymbol? GetThrownExceptionType(this SemanticModel model, ExpressionSyntax exprSyn)
 		=> exprSyn is ObjectCreationExpressionSyntax
 			? model.GetTypeInfo(exprSyn).Type
@@ -28,6 +87,9 @@ public static class RoslynUtils
 		return model.GetTypeInfo(syn is ArgumentSyntax argSyn ? argSyn.Expression : syn, cancellationToken);
 	}
 
+	public static bool IsEmpty(this SyntaxToken token)
+		=> token.ToString().Length is 0;
+
 	public static bool Matches(this ISymbol expected, ISymbol? actual)
 		=> SymbolEqualityComparer.Default.Equals(expected, actual);
 
@@ -42,4 +104,18 @@ public static class RoslynUtils
 		return expected.Matches(actual as ISymbol);
 	}
 #endif
+
+	public static IEnumerable<AttributeSyntax> Matching(
+		this SyntaxList<AttributeListSyntax> list,
+		INamedTypeSymbol targetAttrSym,
+		SemanticModel semanticModel,
+		CancellationToken cancellationToken)
+			=> list.SelectMany(static als => als.Attributes)
+				.Where(aSyn => targetAttrSym.Matches(semanticModel.GetTypeInfo(aSyn, cancellationToken).Type));
+
+	public static IEnumerable<AttributeSyntax> Matching(
+		this SyntaxList<AttributeListSyntax> list,
+		INamedTypeSymbol targetAttrSym,
+		SyntaxNodeAnalysisContext snac)
+			=> list.Matching(targetAttrSym, snac.SemanticModel, snac.CancellationToken);
 }
diff --git a/ExternalProjects/BizHawk.Analyzer/DefineCheckedOpAnalyzer.cs b/ExternalProjects/BizHawk.Analyzer/DefineCheckedOpAnalyzer.cs
new file mode 100644
index 0000000000..f16f614e2e
--- /dev/null
+++ b/ExternalProjects/BizHawk.Analyzer/DefineCheckedOpAnalyzer.cs
@@ -0,0 +1,85 @@
+namespace BizHawk.Analyzers;
+
+using System.Collections.Generic;
+using System.Collections.Immutable;
+using System.Linq;
+
+[DiagnosticAnalyzer(LanguageNames.CSharp)]
+public sealed class DefineCheckedOpAnalyzer : DiagnosticAnalyzer
+{
+	private const string ERR_MSG_DEPRECATE = "consider marking this unchecked operator as [Obsolete]";
+
+	private const string ERR_MSG_MAKE_CHECKED = "define a checked version of this operator";
+
+	private static readonly DiagnosticDescriptor DiagDefineCheckedOp = new(
+		id: "BHI1300",
+		title: "Declare checked operators",
+		messageFormat: "{0}",
+		category: "Usage",
+		defaultSeverity: DiagnosticSeverity.Warning,
+		isEnabledByDefault: true);
+
+	private static readonly Dictionary<string, string> UncheckedOps = new()
+	{
+		[WellKnownMemberNames.AdditionOperatorName] = WellKnownMemberNames.CheckedAdditionOperatorName,
+		[WellKnownMemberNames.DecrementOperatorName] = WellKnownMemberNames.CheckedDecrementOperatorName,
+		[WellKnownMemberNames.DivisionOperatorName] = WellKnownMemberNames.CheckedDivisionOperatorName,
+		[WellKnownMemberNames.ExplicitConversionName] = WellKnownMemberNames.CheckedExplicitConversionName,
+		[WellKnownMemberNames.IncrementOperatorName] = WellKnownMemberNames.CheckedIncrementOperatorName,
+		[WellKnownMemberNames.MultiplyOperatorName] = WellKnownMemberNames.CheckedMultiplyOperatorName,
+		[WellKnownMemberNames.SubtractionOperatorName] = WellKnownMemberNames.CheckedSubtractionOperatorName,
+		[WellKnownMemberNames.UnaryNegationOperatorName] = WellKnownMemberNames.CheckedUnaryNegationOperatorName,
+	};
+
+	public override ImmutableArray<DiagnosticDescriptor> SupportedDiagnostics { get; }
+		= ImmutableArray.Create(/*HawkSourceAnalyzer.DiagWTF,*/ DiagDefineCheckedOp);
+
+	public override void Initialize(AnalysisContext context)
+	{
+		context.ConfigureGeneratedCodeAnalysis(GeneratedCodeAnalysisFlags.None);
+		context.EnableConcurrentExecution();
+		INamedTypeSymbol? obsoleteAttrSym = null;
+		context.RegisterSyntaxNodeAction(
+			snac =>
+			{
+				obsoleteAttrSym ??= snac.Compilation.GetTypeByMetadataName("System.ObsoleteAttribute")!;
+				bool HasCheckedCounterpart<T>(SyntaxNode node, string checkedName, Func<T, string> getMethodName)
+					=> ((TypeDeclarationSyntax) node.Parent!).Members.OfType<T>() //TODO don't think this accounts for `partial` types
+						.Any(syn => checkedName.Equals(getMethodName(syn), StringComparison.Ordinal));
+				void SuggestDeprecation(SyntaxNode node)
+					=> DiagDefineCheckedOp.ReportAt(node, DiagnosticSeverity.Warning, snac, ERR_MSG_DEPRECATE);
+				switch (snac.Node)
+				{
+					case ConversionOperatorDeclarationSyntax cods:
+						if (UncheckedOps.TryGetValue(cods.GetMethodName(), out var checkedName))
+						{
+							var hasCheckedCounterpart = HasCheckedCounterpart<ConversionOperatorDeclarationSyntax>(
+								cods,
+								checkedName,
+								RoslynUtils.GetMethodName);
+							if (!hasCheckedCounterpart) DiagDefineCheckedOp.ReportAt(cods, snac, ERR_MSG_MAKE_CHECKED);
+							else if (!cods.AttributeLists.Matching(obsoleteAttrSym, snac).Any()) SuggestDeprecation(cods);
+							// else you did it good job
+						}
+						break;
+					case OperatorDeclarationSyntax ods:
+						if (UncheckedOps.TryGetValue(ods.GetMethodName(), out var checkedName1))
+						{
+							var hasCheckedCounterpart = HasCheckedCounterpart<OperatorDeclarationSyntax>(
+								ods,
+								checkedName1,
+								RoslynUtils.GetMethodName);
+							if (!hasCheckedCounterpart) DiagDefineCheckedOp.ReportAt(ods, snac, ERR_MSG_MAKE_CHECKED);
+							else if (!ods.AttributeLists.Matching(obsoleteAttrSym, snac).Any()) SuggestDeprecation(ods);
+							// else you did it good job
+						}
+						break;
+					default:
+						HawkSourceAnalyzer.ReportWTF(snac.Node, snac, message: $"[{nameof(DefineCheckedOpAnalyzer)}] unexpected node kind {snac.Node.GetType().FullName}");
+						break;
+				}
+			},
+			SyntaxKind.ConversionOperatorDeclaration,
+			SyntaxKind.OperatorDeclaration);
+	}
+}
diff --git a/ExternalProjects/BizHawk.Analyzer/FeatureNotImplementedAnalyzer.cs b/ExternalProjects/BizHawk.Analyzer/FeatureNotImplementedAnalyzer.cs
index 2d64ff198c..f0c91605e1 100644
--- a/ExternalProjects/BizHawk.Analyzer/FeatureNotImplementedAnalyzer.cs
+++ b/ExternalProjects/BizHawk.Analyzer/FeatureNotImplementedAnalyzer.cs
@@ -44,8 +44,7 @@ public sealed class FeatureNotImplementedAnalyzer : DiagnosticAnalyzer
 						// else correct usage, do not flag
 					}
 					bool IncludesFNIAttribute(SyntaxList<AttributeListSyntax> mds)
-						=> mds.SelectMany(static als => als.Attributes)
-							.Any(aSyn => featureNotImplementedAttrSym.Matches(snac.SemanticModel.GetTypeInfo(aSyn, snac.CancellationToken).Type));
+						=> mds.Matching(featureNotImplementedAttrSym, snac).Any();
 					void CheckBlockBody(BlockSyntax bs, Location location)
 					{
 						if (bs.Statements is [ ThrowStatementSyntax tss ]) MaybeReportFor(snac.SemanticModel.GetThrownExceptionType(tss), tss);
diff --git a/ExternalProjects/BizHawk.AnalyzersTests/BizHawk.Analyzer/DefineCheckedOpAnalyzerTests.cs b/ExternalProjects/BizHawk.AnalyzersTests/BizHawk.Analyzer/DefineCheckedOpAnalyzerTests.cs
new file mode 100644
index 0000000000..e5ba526a66
--- /dev/null
+++ b/ExternalProjects/BizHawk.AnalyzersTests/BizHawk.Analyzer/DefineCheckedOpAnalyzerTests.cs
@@ -0,0 +1,79 @@
+namespace BizHawk.Tests.Analyzers;
+
+using Verify = Microsoft.CodeAnalysis.CSharp.Testing.CSharpAnalyzerVerifier<
+	BizHawk.Analyzers.DefineCheckedOpAnalyzer,
+	Microsoft.CodeAnalysis.Testing.DefaultVerifier>;
+
+[TestClass]
+public sealed class DefineCheckedOpAnalyzerTests
+{
+	[TestMethod]
+	public Task CheckMisuseOfCheckedOperatorOverloading()
+		=> Verify.VerifyAnalyzerAsync("""
+			/* very much a sample; real numeric types should follow these rules according to [the docs](https://learn.microsoft.com/en-us/dotnet/csharp/language-reference/operators/arithmetic-operators#user-defined-checked-operators):
+			 * - A checked operator throws an OverflowException.
+			 * - An operator without the checked modifier returns an instance representing a truncated result.
+			 * I didn't do any of that, I just came up with something that threw and something that didn't and called it a day --yoshi
+			 */
+			using System;
+			public struct GF7 {
+				private static readonly int[] Inverses = [ -1, 1, 4, 5, 2, 3, 6 ];
+				public static GF7 operator checked -(GF7 x) => new(-x._value); // the most useless but here for completeness
+				{|BHI1300:public static GF7 operator /*unchecked*/ -(GF7 x) => new(-x._value % 7);|}
+				public static GF7 operator checked ++(GF7 x) => new(x._value + 1);
+				{|BHI1300:public static GF7 operator /*unchecked*/ ++(GF7 x) => new((x._value + 1) % 7);|}
+				public static GF7 operator checked --(GF7 x) => new(x._value - 1);
+				{|BHI1300:public static GF7 operator /*unchecked*/ --(GF7 x) => new((x._value - 1) % 7);|}
+				public static GF7 operator checked +(GF7 x, GF7 y) => new(x._value + y._value);
+				{|BHI1300:public static GF7 operator /*unchecked*/ +(GF7 x, GF7 y) => new((x._value + y._value) % 7);|}
+				public static GF7 operator checked +(GF7 x, int y) => new(x._value + y);
+				{|BHI1300:public static GF7 operator /*unchecked*/ +(GF7 x, int y) => new((x._value + y) % 7);|}
+				public static GF7 operator checked -(GF7 minuend, int subtrahend) => new(minuend._value - subtrahend);
+				{|BHI1300:public static GF7 operator /*unchecked*/ -(GF7 minuend, int subtrahend) => new((minuend._value - subtrahend) % 7);|}
+				public static GF7 operator checked *(GF7 x, int y) => new(x._value * y);
+				{|BHI1300:public static GF7 operator /*unchecked*/ *(GF7 x, int y) => new((x._value * y) % 7);|}
+				public static GF7 operator checked /(GF7 dividend, GF7 divisor) => new((dividend._value * Inverses[divisor._value]) % 7);
+				{|BHI1300:public static GF7 operator /*unchecked*/ /(GF7 dividend, GF7 divisor) => divisor._value is 0 ? default : new((dividend._value * Inverses[divisor._value]) % 7);|}
+				public static explicit operator checked GF7(int n) => new(n);
+				{|BHI1300:public static explicit operator /*unchecked*/ GF7(int n) => new(n % 7);|}
+				private byte _value;
+				public byte Value {
+					get => _value;
+					set {
+						if (value < 0 || 6 < value) throw new ArgumentOutOfRangeException(paramName: nameof(value), value, message: "must be in 0..<7");
+						_value = value;
+					}
+				}
+				public GF7(byte value) => Value = value;
+				private GF7(int value) => Value = unchecked((byte) value);
+			}
+		""");
+
+	[TestMethod]
+	public Task CheckMisuseOfUncheckedOperatorOverloading()
+		=> Verify.VerifyAnalyzerAsync("""
+			using System;
+			public struct GF7 {
+				private static readonly int[] Inverses = [ -1, 1, 4, 5, 2, 3, 6 ];
+				{|BHI1300:public static GF7 operator -(GF7 x) => new(-x._value % 7);|}
+				{|BHI1300:public static GF7 operator ++(GF7 x) => new((x._value + 1) % 7);|}
+				{|BHI1300:public static GF7 operator --(GF7 x) => new((x._value - 1) % 7);|}
+				{|BHI1300:public static GF7 operator +(GF7 x, GF7 y) => new((x._value + y._value) % 7);|}
+				{|BHI1300:public static GF7 operator +(GF7 x, int y) => new((x._value + y) % 7);|}
+				{|BHI1300:public static GF7 operator -(GF7 minuend, int subtrahend) => new((minuend._value - subtrahend) % 7);|}
+				{|BHI1300:public static GF7 operator *(GF7 x, int y) => new((x._value * y) % 7);|}
+				{|BHI1300:public static GF7 operator /(GF7 dividend, GF7 divisor) => divisor._value is 0 ? default : new((dividend._value * Inverses[divisor._value]) % 7);|}
+				{|BHI1300:public static explicit operator GF7(int n) => new(n % 7);|}
+				private byte _value;
+				public byte Value {
+					get => _value;
+					set {
+						if (value < 0 || 6 < value) throw new ArgumentOutOfRangeException(paramName: nameof(value), value, message: "must be in 0..<7");
+						_value = value;
+					}
+				}
+				public GF7(byte value) => Value = value;
+				private GF7(int value) => Value = unchecked((byte) value);
+			}
+		""");
+}
diff --git a/References/BizHawk.Analyzer.dll b/References/BizHawk.Analyzer.dll
index 55fc503de8..17c066a187 100644
Binary files a/References/BizHawk.Analyzer.dll and b/References/BizHawk.Analyzer.dll differ
diff --git a/src/BizHawk.Common/Win32/ShellLinkImports.cs b/src/BizHawk.Common/Win32/ShellLinkImports.cs
index dc8036523d..797f899b88 100644
--- a/src/BizHawk.Common/Win32/ShellLinkImports.cs
+++ b/src/BizHawk.Common/Win32/ShellLinkImports.cs
@@ -1,4 +1,5 @@
 #nullable disable
+#pragma warning disable BHI1300 // explicit conversion operators w/ no checked variant
 
 using System.Runtime.CompilerServices;
 using System.Runtime.InteropServices;