diff --git a/extensions/git/src/commands.ts b/extensions/git/src/commands.ts
index b8ec3382b63..913627c8922 100644
--- a/extensions/git/src/commands.ts
+++ b/extensions/git/src/commands.ts
@@ -14,7 +14,7 @@ import { Model } from './model';
 import { Repository, Resource, ResourceGroupType } from './repository';
 import { applyLineChanges, getModifiedRange, intersectDiffWithRange, invertLineChange, toLineRanges } from './staging';
 import { fromGitUri, toGitUri, isGitUri } from './uri';
-import { grep, isDescendant, logTimestamp, pathEquals } from './util';
+import { grep, isDescendant, logTimestamp, pathEquals, relativePath } from './util';
 import { Log, LogLevel } from './log';
 import { GitTimelineItem } from './timelineProvider';
 import { ApiRepository } from './api/api1';
@@ -803,7 +803,7 @@ export class CommandCenter {
 			return;
 		}
 
-		const from = path.relative(repository.root, fromUri.fsPath);
+		const from = relativePath(repository.root, fromUri.fsPath);
 		let to = await window.showInputBox({
 			value: from,
 			valueSelection: [from.length - path.basename(from).length, from.length]
diff --git a/extensions/git/src/repository.ts b/extensions/git/src/repository.ts
index a2e8fd1a800..6b2205ddcb7 100644
--- a/extensions/git/src/repository.ts
+++ b/extensions/git/src/repository.ts
@@ -14,7 +14,7 @@ import { debounce, memoize, throttle } from './decorators';
 import { Commit, GitError, Repository as BaseRepository, Stash, Submodule, LogFileOptions } from './git';
 import { StatusBarCommands } from './statusbar';
 import { toGitUri } from './uri';
-import { anyEvent, combinedDisposable, debounceEvent, dispose, EmptyDisposable, eventToPromise, filterEvent, find, IDisposable, isDescendant, logTimestamp, onceEvent } from './util';
+import { anyEvent, combinedDisposable, debounceEvent, dispose, EmptyDisposable, eventToPromise, filterEvent, find, IDisposable, isDescendant, logTimestamp, onceEvent, relativePath } from './util';
 import { IFileWatcher, watch } from './watch';
 import { Log, LogLevel } from './log';
 import { IPushErrorHandlerRegistry } from './pushError';
@@ -1161,8 +1161,8 @@ export class Repository implements Disposable {
 	}
 
 	async stage(resource: Uri, contents: string): Promise<void> {
-		const relativePath = path.relative(this.repository.root, resource.fsPath).replace(/\\/g, '/');
-		await this.run(Operation.Stage, () => this.repository.stage(relativePath, contents));
+		const path = relativePath(this.repository.root, resource.fsPath).replace(/\\/g, '/');
+		await this.run(Operation.Stage, () => this.repository.stage(path, contents));
 		this._onDidChangeOriginalResource.fire(resource);
 	}
 
@@ -1545,16 +1545,16 @@ export class Repository implements Disposable {
 
 	async show(ref: string, filePath: string): Promise<string> {
 		return await this.run(Operation.Show, async () => {
-			const relativePath = path.relative(this.repository.root, filePath).replace(/\\/g, '/');
+			const path = relativePath(this.repository.root, filePath).replace(/\\/g, '/');
 			const configFiles = workspace.getConfiguration('files', Uri.file(filePath));
 			const defaultEncoding = configFiles.get<string>('encoding');
 			const autoGuessEncoding = configFiles.get<boolean>('autoGuessEncoding');
 
 			try {
-				return await this.repository.bufferString(`${ref}:${relativePath}`, defaultEncoding, autoGuessEncoding);
+				return await this.repository.bufferString(`${ref}:${path}`, defaultEncoding, autoGuessEncoding);
 			} catch (err) {
 				if (err.gitErrorCode === GitErrorCodes.WrongCase) {
-					const gitRelativePath = await this.repository.getGitRelativePath(ref, relativePath);
+					const gitRelativePath = await this.repository.getGitRelativePath(ref, path);
 					return await this.repository.bufferString(`${ref}:${gitRelativePath}`, defaultEncoding, autoGuessEncoding);
 				}
 
@@ -1565,8 +1565,8 @@ export class Repository implements Disposable {
 
 	async buffer(ref: string, filePath: string): Promise<Buffer> {
 		return this.run(Operation.Show, () => {
-			const relativePath = path.relative(this.repository.root, filePath).replace(/\\/g, '/');
-			return this.repository.buffer(`${ref}:${relativePath}`);
+			const path = relativePath(this.repository.root, filePath).replace(/\\/g, '/');
+			return this.repository.buffer(`${ref}:${path}`);
 		});
 	}
 
@@ -1610,7 +1610,7 @@ export class Repository implements Disposable {
 		return await this.run(Operation.Ignore, async () => {
 			const ignoreFile = `${this.repository.root}${path.sep}.gitignore`;
 			const textToAppend = files
-				.map(uri => path.relative(this.repository.root, uri.fsPath).replace(/\\/g, '/'))
+				.map(uri => relativePath(this.repository.root, uri.fsPath).replace(/\\/g, '/'))
 				.join('\n');
 
 			const document = await new Promise(c => fs.exists(ignoreFile, c))
diff --git a/extensions/git/src/util.ts b/extensions/git/src/util.ts
index 7631dbe4727..a8ae8fff98a 100644
--- a/extensions/git/src/util.ts
+++ b/extensions/git/src/util.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { Event, Disposable, EventEmitter } from 'vscode';
-import { dirname, sep } from 'path';
+import { dirname, sep, relative } from 'path';
 import { Readable } from 'stream';
 import { promises as fs, createReadStream } from 'fs';
 import * as byline from 'byline';
@@ -287,6 +287,16 @@ export function detectUnicodeEncoding(buffer: Buffer): Encoding | null {
 	return null;
 }
 
+function normalizePath(path: string): string {
+	// Windows & Mac are currently being handled
+	// as case insensitive file systems in VS Code.
+	if (isWindows || isMacintosh) {
+		return path.toLowerCase();
+	}
+
+	return path;
+}
+
 export function isDescendant(parent: string, descendant: string): boolean {
 	if (parent === descendant) {
 		return true;
@@ -296,25 +306,26 @@ export function isDescendant(parent: string, descendant: string): boolean {
 		parent += sep;
 	}
 
-	// Windows & Mac are currently being handled
-	// as case insensitive file systems in VS Code.
-	if (isWindows || isMacintosh) {
-		parent = parent.toLowerCase();
-		descendant = descendant.toLowerCase();
-	}
-
-	return descendant.startsWith(parent);
+	return normalizePath(descendant).startsWith(normalizePath(parent));
 }
 
 export function pathEquals(a: string, b: string): boolean {
-	// Windows & Mac are currently being handled
-	// as case insensitive file systems in VS Code.
-	if (isWindows || isMacintosh) {
-		a = a.toLowerCase();
-		b = b.toLowerCase();
+	return normalizePath(a) === normalizePath(b);
+}
+
+/**
+ * Given the `repository.root` compute the relative path while trying to preserve
+ * the casing of the resource URI. The `repository.root` segment of the path can
+ * have a casing mismatch if the folder/workspace is being opened with incorrect
+ * casing.
+ */
+export function relativePath(from: string, to: string): string {
+	if (isDescendant(from, to) && from.length < to.length) {
+		return to.substring(from.length + 1);
 	}
 
-	return a === b;
+	// Fallback to `path.relative`
+	return relative(from, to);
 }
 
 export function* splitInChunks(array: string[], maxChunkLength: number): IterableIterator<string[]> {