diff --git a/src/LuaPrinter.ts b/src/LuaPrinter.ts
index 65c33b88a..4bfe53f5c 100644
--- a/src/LuaPrinter.ts
+++ b/src/LuaPrinter.ts
@@ -1,11 +1,13 @@
+import * as path from "path";
 import { Mapping, SourceMapGenerator, SourceNode } from "source-map";
+import { getEmitPath } from ".";
 import * as ts from "typescript";
 import { CompilerOptions, isBundleEnabled, LuaLibImportKind } from "./CompilerOptions";
 import * as lua from "./LuaAST";
 import { loadLuaLibFeatures, LuaLibFeature } from "./LuaLib";
 import { isValidLuaIdentifier } from "./transformation/utils/safe-names";
 import { EmitHost } from "./transpilation";
-import { intersperse, trimExtension } from "./utils";
+import { intersperse, normalizeSlashes } from "./utils";
 
 // https://www.lua.org/pil/2.4.html
 // https://www.ecma-international.org/ecma-262/10.0/index.html#table-34
@@ -120,14 +122,17 @@ export class LuaPrinter {
     };
 
     private currentIndent = "";
-    private sourceFile: string;
+    private luaFile: string;
+    private relativeSourcePath: string;
     private options: CompilerOptions;
 
     public static readonly sourceMapTracebackPlaceholder = "{#SourceMapTraceback}";
 
-    constructor(private emitHost: EmitHost, program: ts.Program, fileName: string) {
+    constructor(private emitHost: EmitHost, private program: ts.Program, private sourceFile: string) {
         this.options = program.getCompilerOptions();
-        this.sourceFile = fileName;
+        this.luaFile = normalizeSlashes(getEmitPath(this.sourceFile, this.program));
+        // Source nodes contain relative path from mapped lua file to original TS source file
+        this.relativeSourcePath = normalizeSlashes(path.relative(path.dirname(this.luaFile), this.sourceFile));
     }
 
     public print(file: lua.File): PrintResult {
@@ -230,12 +235,12 @@ export class LuaPrinter {
         const { line, column } = lua.getOriginalPos(node);
 
         return line !== undefined && column !== undefined
-            ? new SourceNode(line + 1, column, this.sourceFile, chunks, name)
-            : new SourceNode(null, null, this.sourceFile, chunks, name);
+            ? new SourceNode(line + 1, column, this.relativeSourcePath, chunks, name)
+            : new SourceNode(null, null, this.relativeSourcePath, chunks, name);
     }
 
     protected concatNodes(...chunks: SourceChunk[]): SourceNode {
-        return new SourceNode(null, null, this.sourceFile, chunks);
+        return new SourceNode(null, null, this.relativeSourcePath, chunks);
     }
 
     protected printBlock(block: lua.Block): SourceNode {
@@ -757,7 +762,7 @@ export class LuaPrinter {
     }
 
     public printOperator(kind: lua.Operator): SourceNode {
-        return new SourceNode(null, null, this.sourceFile, LuaPrinter.operatorMap[kind]);
+        return new SourceNode(null, null, this.relativeSourcePath, LuaPrinter.operatorMap[kind]);
     }
 
     protected joinChunksWithComma(chunks: SourceChunk[]): SourceChunk[] {
@@ -787,7 +792,7 @@ export class LuaPrinter {
     // will not generate 'empty' mappings in the source map that point to nothing in the original TS.
     private buildSourceMap(sourceRoot: string, rootSourceNode: SourceNode): SourceMapGenerator {
         const map = new SourceMapGenerator({
-            file: trimExtension(this.sourceFile) + ".lua",
+            file: path.basename(this.luaFile),
             sourceRoot,
         });
 
diff --git a/src/transpilation/diagnostics.ts b/src/transpilation/diagnostics.ts
index 098d78740..0aa772cd3 100644
--- a/src/transpilation/diagnostics.ts
+++ b/src/transpilation/diagnostics.ts
@@ -8,7 +8,7 @@ const createDiagnosticFactory = <TArgs extends any[]>(
 
 export const couldNotResolveRequire = createDiagnosticFactory(
     (requirePath: string, containingFile: string) =>
-        `Could not resolve require path '${requirePath}' in file ${containingFile}.`
+        `Could not resolve lua source files for require path '${requirePath}' in file ${containingFile}.`
 );
 
 export const couldNotReadDependency = createDiagnosticFactory(
diff --git a/test/unit/modules/__snapshots__/resolution.spec.ts.snap b/test/unit/modules/__snapshots__/resolution.spec.ts.snap
index 4db74c57f..a250dbd46 100644
--- a/test/unit/modules/__snapshots__/resolution.spec.ts.snap
+++ b/test/unit/modules/__snapshots__/resolution.spec.ts.snap
@@ -7,4 +7,4 @@ local ____ = module
 return ____exports"
 `;
 
-exports[`doesn't resolve paths out of root dir: diagnostics 1`] = `"error TSTL: Could not resolve require path '../module' in file main.ts."`;
+exports[`doesn't resolve paths out of root dir: diagnostics 1`] = `"error TSTL: Could not resolve lua source files for require path '../module' in file main.ts."`;
diff --git a/test/unit/printer/sourcemaps.spec.ts b/test/unit/printer/sourcemaps.spec.ts
index 6c5857120..fdc21a13a 100644
--- a/test/unit/printer/sourcemaps.spec.ts
+++ b/test/unit/printer/sourcemaps.spec.ts
@@ -163,25 +163,35 @@ test.each([
 });
 
 test.each([
-    { fileName: "/proj/foo.ts", config: {} },
+    {
+        fileName: "/proj/foo.ts",
+        config: {},
+        expectedSourcePath: "foo.ts", // ts and lua will be emitted to same directory
+    },
     {
         fileName: "/proj/src/foo.ts",
-        config: { outDir: "/proj/dst" },
+        config: {
+            outDir: "/proj/dst",
+        },
+        expectedSourcePath: "../src/foo.ts", // path from proj/dst outDir to proj/src/foo.ts
     },
     {
         fileName: "/proj/src/foo.ts",
         config: { rootDir: "/proj/src", outDir: "/proj/dst" },
+        expectedSourcePath: "../src/foo.ts", // path from proj/dst outDir to proj/src/foo.ts
     },
     {
         fileName: "/proj/src/sub/foo.ts",
         config: { rootDir: "/proj/src", outDir: "/proj/dst" },
+        expectedSourcePath: "../../src/sub/foo.ts", // path from proj/dst/sub outDir to proj/src/sub/foo.ts
     },
     {
         fileName: "/proj/src/sub/main.ts",
-        config: { rootDir: "/proj/src", outDir: "/proj/dst", sourceRoot: "bin" },
-        fullSource: "bin/proj/src/sub/main.ts",
+        config: { rootDir: "/proj/src", outDir: "/proj/dst", sourceRoot: "bin/binsub/binsubsub" },
+        expectedSourcePath: "../../src/sub/main.ts", // path from proj/dst/sub outDir to proj/src/sub/foo.ts
+        fullSource: "bin/src/sub/main.ts",
     },
-])("Source map has correct sources (%p)", async ({ fileName, config, fullSource }) => {
+])("Source map has correct sources (%p)", async ({ fileName, config, fullSource, expectedSourcePath }) => {
     const file = util.testModule`
         const foo = "foo"
     `
@@ -191,11 +201,11 @@ test.each([
 
     const sourceMap = JSON.parse(file.luaSourceMap);
     expect(sourceMap.sources).toHaveLength(1);
-    expect(sourceMap.sources[0]).toBe(fileName);
+    expect(sourceMap.sources[0]).toBe(expectedSourcePath);
 
     const consumer = await new SourceMapConsumer(file.luaSourceMap);
     expect(consumer.sources).toHaveLength(1);
-    expect(consumer.sources[0]).toBe(fullSource ?? fileName);
+    expect(consumer.sources[0]).toBe(fullSource ?? expectedSourcePath);
 });
 
 test.each([