diff --git a/src/commands/diffWithRevision.ts b/src/commands/diffWithRevision.ts
index 3936285..78c3f72 100644
--- a/src/commands/diffWithRevision.ts
+++ b/src/commands/diffWithRevision.ts
@@ -1,7 +1,7 @@
 'use strict';
 import { TextDocumentShowOptions, TextEditor, Uri } from 'vscode';
 import { ActiveEditorCommand, command, Commands, executeCommand, getCommandUri } from './common';
-import { GlyphChars } from '../constants';
+import { GlyphChars, quickPickTitleMaxChars } from '../constants';
 import { Container } from '../container';
 import { DiffWithCommandArgs } from './diffWith';
 import { GitRevision } from '../git/git';
@@ -44,10 +44,12 @@ export class DiffWithRevisionCommand extends ActiveEditorCommand {
 							: undefined),
 				);
 
+			const title = `Open Changes with Revision${Strings.pad(GlyphChars.Dot, 2, 2)}`;
 			const pick = await CommitPicker.show(
 				log,
-				`Open Changes with Revision${Strings.pad(GlyphChars.Dot, 2, 2)}${gitUri.getFormattedPath({
+				`${title}${gitUri.getFormattedFilename({
 					suffix: gitUri.sha ? `:${GitRevision.shorten(gitUri.sha)}` : undefined,
+					truncateTo: quickPickTitleMaxChars - title.length,
 				})}`,
 				'Choose a commit to compare with',
 				{
diff --git a/src/commands/diffWithRevisionFrom.ts b/src/commands/diffWithRevisionFrom.ts
index 166f9c8..92febc2 100644
--- a/src/commands/diffWithRevisionFrom.ts
+++ b/src/commands/diffWithRevisionFrom.ts
@@ -2,7 +2,7 @@
 import * as paths from 'path';
 import { TextDocumentShowOptions, TextEditor, Uri } from 'vscode';
 import { ActiveEditorCommand, command, Commands, executeCommand, getCommandUri } from './common';
-import { GlyphChars } from '../constants';
+import { GlyphChars, quickPickTitleMaxChars } from '../constants';
 import { Container } from '../container';
 import { DiffWithCommandArgs } from './diffWith';
 import { GitReference, GitRevision } from '../git/git';
@@ -38,9 +38,10 @@ export class DiffWithRevisionFromCommand extends ActiveEditorCommand {
 			args.line = editor?.selection.active.line ?? 0;
 		}
 
+		const title = `Open Changes with Branch or Tag${Strings.pad(GlyphChars.Dot, 2, 2)}`;
 		const pick = await ReferencePicker.show(
 			gitUri.repoPath,
-			`Open Changes with Branch or Tag${Strings.pad(GlyphChars.Dot, 2, 2)}${gitUri.getFormattedPath()}`,
+			`${title}${gitUri.getFormattedFilename({ truncateTo: quickPickTitleMaxChars - title.length })}`,
 			'Choose a branch or tag to compare with',
 			{
 				allowEnteringRefs: true,
diff --git a/src/commands/git/log.ts b/src/commands/git/log.ts
index fcbf7b0..be1b2c7 100644
--- a/src/commands/git/log.ts
+++ b/src/commands/git/log.ts
@@ -12,7 +12,7 @@ import {
 	StepResult,
 	StepState,
 } from '../quickCommand';
-import { GlyphChars } from '../../constants';
+import { GlyphChars, quickPickTitleMaxChars } from '../../constants';
 import { GitUri } from '../../git/gitUri';
 import { Strings } from '../../system';
 
@@ -128,19 +128,17 @@ export class LogGitCommand extends QuickCommand<State> {
 				context.selectedBranchOrTag = state.reference;
 			}
 
-			context.title = `${this.title}${Strings.pad(GlyphChars.Dot, 2, 2)}${GitReference.toString(
-				context.selectedBranchOrTag,
-				{
-					icon: false,
-				},
-			)}${
-				state.fileName
-					? `${Strings.pad(GlyphChars.Dot, 2, 2)}${GitUri.getFormattedPath(state.fileName, {
-							relativeTo: state.repo.path,
-							truncateTo: 35,
-					  })}`
-					: ''
-			}`;
+			context.title = `${this.title}${Strings.pad(
+				GlyphChars.Dot,
+				2,
+				2,
+			)}${GitReference.toString(context.selectedBranchOrTag, { icon: false })}`;
+
+			if (state.fileName) {
+				context.title += `${Strings.pad(GlyphChars.Dot, 2, 2)}${GitUri.getFormattedFilename(state.fileName, {
+					truncateTo: quickPickTitleMaxChars - context.title.length - 3,
+				})}`;
+			}
 
 			if (state.counter < 3 && context.selectedBranchOrTag != null) {
 				const ref = context.selectedBranchOrTag.ref;
diff --git a/src/commands/git/stash.ts b/src/commands/git/stash.ts
index f2ead4b..adaf530 100644
--- a/src/commands/git/stash.ts
+++ b/src/commands/git/stash.ts
@@ -1,5 +1,6 @@
 'use strict';
 import { QuickInputButtons, QuickPickItem, Uri, window } from 'vscode';
+import { GlyphChars } from '../../constants';
 import { Container } from '../../container';
 import { GitReference, GitStashCommit, GitStashReference, Repository } from '../../git/git';
 import { GitUri } from '../../git/gitUri';
@@ -21,6 +22,7 @@ import {
 import { FlagsQuickPickItem, QuickPickItemOfT } from '../../quickpicks';
 import { Logger } from '../../logger';
 import { Messages } from '../../messages';
+import { Strings } from '../../system';
 
 interface Context {
 	repos: Repository[];
@@ -506,7 +508,18 @@ export class StashGitCommand extends QuickCommand<State> {
 
 	private async *pushCommandInputMessageStep(state: PushStepState, context: Context): StepResultGenerator<string> {
 		const step = QuickCommand.createInputStep({
-			title: appendReposToTitle(context.title, state, context),
+			title: appendReposToTitle(
+				context.title,
+				state,
+				context,
+				state.uris != null
+					? `${Strings.pad(GlyphChars.Dot, 2, 2)}${
+							state.uris.length === 1
+								? GitUri.getFormattedFilename(state.uris[0])
+								: `${state.uris.length} files`
+					  }`
+					: undefined,
+			),
 			placeholder: 'Please provide a stash message',
 			value: state.message,
 			prompt: 'Enter stash message',
@@ -546,17 +559,17 @@ export class StashGitCommand extends QuickCommand<State> {
 				: [
 						FlagsQuickPickItem.create<PushFlags>(state.flags, [], {
 							label: context.title,
-							detail: `Will stash changes in ${
+							detail: `Will stash changes from ${
 								state.uris.length === 1
-									? GitUri.getFormattedPath(state.uris[0], { relativeTo: state.repo.path })
+									? GitUri.getFormattedFilename(state.uris[0])
 									: `${state.uris.length} files`
 							}`,
 						}),
 						FlagsQuickPickItem.create<PushFlags>(state.flags, ['--keep-index'], {
 							label: `${context.title} & Keep Staged`,
-							detail: `Will stash changes in ${
+							detail: `Will stash changes from ${
 								state.uris.length === 1
-									? GitUri.getFormattedPath(state.uris[0], { relativeTo: state.repo.path })
+									? GitUri.getFormattedFilename(state.uris[0])
 									: `${state.uris.length} files`
 							}, but will keep staged files intact`,
 						}),
diff --git a/src/commands/openFileAtRevision.ts b/src/commands/openFileAtRevision.ts
index 1fe41c4..4e6da21 100644
--- a/src/commands/openFileAtRevision.ts
+++ b/src/commands/openFileAtRevision.ts
@@ -2,7 +2,7 @@
 import { TextDocumentShowOptions, TextEditor, Uri } from 'vscode';
 import { ActiveEditorCommand, command, Commands, getCommandUri } from './common';
 import { FileAnnotationType } from '../configuration';
-import { GlyphChars } from '../constants';
+import { GlyphChars, quickPickTitleMaxChars } from '../constants';
 import { Container } from '../container';
 import { GitRevision } from '../git/git';
 import { GitUri } from '../git/gitUri';
@@ -72,10 +72,12 @@ export class OpenFileAtRevisionCommand extends ActiveEditorCommand {
 								: undefined),
 					);
 
+				const title = `Open File at Revision${Strings.pad(GlyphChars.Dot, 2, 2)}`;
 				const pick = await CommitPicker.show(
 					log,
-					`Open File at Revision${Strings.pad(GlyphChars.Dot, 2, 2)}${gitUri.getFormattedPath({
+					`${title}${gitUri.getFormattedFilename({
 						suffix: gitUri.sha ? `:${GitRevision.shorten(gitUri.sha)}` : undefined,
+						truncateTo: quickPickTitleMaxChars - title.length,
 					})}`,
 					'Choose a commit to open the file revision from',
 					{
diff --git a/src/commands/openFileAtRevisionFrom.ts b/src/commands/openFileAtRevisionFrom.ts
index 0d0b485..0024c8c 100644
--- a/src/commands/openFileAtRevisionFrom.ts
+++ b/src/commands/openFileAtRevisionFrom.ts
@@ -2,7 +2,7 @@
 import { TextDocumentShowOptions, TextEditor, Uri } from 'vscode';
 import { ActiveEditorCommand, command, Commands, getCommandUri } from './common';
 import { FileAnnotationType } from '../configuration';
-import { GlyphChars } from '../constants';
+import { GlyphChars, quickPickTitleMaxChars } from '../constants';
 import { GitReference } from '../git/git';
 import { GitUri } from '../git/gitUri';
 import { GitActions } from './gitCommands';
@@ -40,9 +40,10 @@ export class OpenFileAtRevisionFromCommand extends ActiveEditorCommand {
 		}
 
 		if (args.reference == null) {
+			const title = `Open File at Revision${Strings.pad(GlyphChars.Dot, 2, 2)}`;
 			const pick = await ReferencePicker.show(
 				gitUri.repoPath,
-				`Open File at Revision${Strings.pad(GlyphChars.Dot, 2, 2)}${gitUri.getFormattedPath()}`,
+				`${title}${gitUri.getFormattedFilename({ truncateTo: quickPickTitleMaxChars - title.length })}`,
 				'Choose a branch or tag to open the file revision from',
 				{
 					allowEnteringRefs: true,
diff --git a/src/commands/quickCommand.steps.ts b/src/commands/quickCommand.steps.ts
index 812710d..7a40125 100644
--- a/src/commands/quickCommand.steps.ts
+++ b/src/commands/quickCommand.steps.ts
@@ -3,7 +3,7 @@ import { QuickInputButton, QuickPick } from 'vscode';
 import { Commands } from './common';
 import { configuration } from '../configuration';
 import { Container } from '../container';
-import { GlyphChars } from '../constants';
+import { GlyphChars, quickPickTitleMaxChars } from '../constants';
 import {
 	GitBranch,
 	GitBranchReference,
@@ -78,17 +78,26 @@ export function appendReposToTitle<
 	State extends { repo: Repository } | { repos: Repository[] },
 	Context extends { repos: Repository[] }
 >(title: string, state: State, context: Context, additionalContext?: string) {
-	if (context.repos.length === 1) return `${title}${additionalContext ?? ''}`;
+	if (context.repos.length === 1) {
+		return `${title}${Strings.truncate(additionalContext ?? '', quickPickTitleMaxChars - title.length)}`;
+	}
 
+	let repoContext;
 	if ((state as { repo: Repository }).repo != null) {
-		return `${title}${Strings.pad(GlyphChars.Dot, 2, 2)}${(state as { repo: Repository }).repo.formattedName}`;
+		repoContext = `${additionalContext ?? ''}${Strings.pad(GlyphChars.Dot, 2, 2)}${
+			(state as { repo: Repository }).repo.formattedName
+		}`;
+	} else if ((state as { repos: Repository[] }).repos.length === 1) {
+		repoContext = `${additionalContext ?? ''}${Strings.pad(GlyphChars.Dot, 2, 2)}${
+			(state as { repos: Repository[] }).repos[0].formattedName
+		}`;
+	} else {
+		repoContext = `${Strings.pad(GlyphChars.Dot, 2, 2)}${
+			(state as { repos: Repository[] }).repos.length
+		} repositories`;
 	}
 
-	return `${title}${Strings.pad(GlyphChars.Dot, 2, 2)}${
-		(state as { repos: Repository[] }).repos.length === 1
-			? `${(state as { repos: Repository[] }).repos[0].formattedName}${additionalContext ?? ''}`
-			: `${(state as { repos: Repository[] }).repos.length} repositories`
-	}`;
+	return `${title}${Strings.truncate(repoContext, quickPickTitleMaxChars - title.length)}`;
 }
 
 export async function getBranches(
@@ -1521,10 +1530,7 @@ export async function* showCommitOrStashFileStep<
 			}),
 			state,
 			context,
-			`${Strings.pad(GlyphChars.Dot, 2, 2)}${GitUri.getFormattedPath(state.fileName, {
-				relativeTo: state.repo.path,
-				truncateTo: 35,
-			})}`,
+			`${Strings.pad(GlyphChars.Dot, 2, 2)}${GitUri.getFormattedFilename(state.fileName)}`,
 		),
 		placeholder: `${GitUri.getFormattedPath(state.fileName, {
 			relativeTo: state.repo.path,
diff --git a/src/constants.ts b/src/constants.ts
index ca9c6ee..50eae5a 100644
--- a/src/constants.ts
+++ b/src/constants.ts
@@ -8,6 +8,8 @@ export const extensionOutputChannelName = 'GitLens';
 export const extensionQualifiedId = `eamodio.${extensionId}`;
 export const extensionTerminalName = 'GitLens';
 
+export const quickPickTitleMaxChars = 80;
+
 export enum BuiltInCommands {
 	CloseActiveEditor = 'workbench.action.closeActiveEditor',
 	CloseAllEditors = 'workbench.action.closeAllEditors',
diff --git a/src/git/formatters/statusFormatter.ts b/src/git/formatters/statusFormatter.ts
index 1ec34df..18be82a 100644
--- a/src/git/formatters/statusFormatter.ts
+++ b/src/git/formatters/statusFormatter.ts
@@ -31,7 +31,10 @@ export class StatusFileFormatter extends Formatter<GitFile, StatusFormatOptions>
 	}
 
 	get filePath() {
-		const filePath = GitFile.getFormattedPath(this._item, { relativeTo: this._options.relativePath });
+		const filePath = GitFile.getFormattedPath(this._item, {
+			relativeTo: this._options.relativePath,
+			truncateTo: this._options.tokenOptions.filePath?.truncateTo,
+		});
 		return this._padOrTruncate(filePath, this._options.tokenOptions.filePath);
 	}
 
diff --git a/src/git/gitUri.ts b/src/git/gitUri.ts
index 09ab353..3e31433 100644
--- a/src/git/gitUri.ts
+++ b/src/git/gitUri.ts
@@ -2,7 +2,7 @@
 import * as paths from 'path';
 import { Uri } from 'vscode';
 import { UriComparer } from '../comparers';
-import { DocumentSchemes, GlyphChars } from '../constants';
+import { DocumentSchemes } from '../constants';
 import { Container } from '../container';
 import { GitCommit, GitFile, GitRevision } from '../git/git';
 import { Logger } from '../logger';
@@ -180,15 +180,12 @@ export class GitUri extends ((Uri as any) as UriEx) {
 		return this.sha === (GitUri.is(uri) ? uri.sha : undefined);
 	}
 
-	getFormattedPath(options: { relativeTo?: string; separator?: string; suffix?: string } = {}): string {
-		const {
-			relativeTo = this.repoPath,
-			separator = Strings.pad(GlyphChars.Dot, 1, 1),
-			suffix = emptyStr,
-		} = options;
+	getFormattedFilename(options: { suffix?: string; truncateTo?: number } = {}): string {
+		return GitUri.getFormattedFilename(this.fsPath, options);
+	}
 
-		const directory = GitUri.getDirectory(this.fsPath, relativeTo);
-		return `${paths.basename(this.fsPath)}${suffix}${directory ? `${separator}${directory}` : emptyStr}`;
+	getFormattedPath(options: { relativeTo?: string; suffix?: string; truncateTo?: number } = {}): string {
+		return GitUri.getFormattedPath(this.fsPath, { relativeTo: this.repoPath, ...options });
 	}
 
 	@memoize()
@@ -330,39 +327,78 @@ export class GitUri extends ((Uri as any) as UriEx) {
 		return directory == null || directory.length === 0 || directory === '.' ? emptyStr : directory;
 	}
 
-	static getFormattedPath(
+	static getFormattedFilename(
 		fileNameOrUri: string | Uri,
-		options: { relativeTo?: string; separator?: string; suffix?: string; truncateTo?: number },
+		options: {
+			suffix?: string;
+			truncateTo?: number;
+		} = {},
 	): string {
-		const { relativeTo, separator = Strings.pad(GlyphChars.Dot, 1, 1), suffix = emptyStr, truncateTo } = options;
+		const { suffix = emptyStr, truncateTo } = options;
 
 		let fileName: string;
 		if (fileNameOrUri instanceof Uri) {
-			if (GitUri.is(fileNameOrUri)) return fileNameOrUri.getFormattedPath(options);
-
 			fileName = fileNameOrUri.fsPath;
 		} else {
 			fileName = fileNameOrUri;
 		}
 
-		const file = `${paths.basename(fileName)}${suffix}`;
-		if (truncateTo != null && file.length > truncateTo) {
+		let file = paths.basename(fileName);
+		if (truncateTo != null && file.length >= truncateTo) {
 			return Strings.truncateMiddle(file, truncateTo);
 		}
 
-		let directory = GitUri.getDirectory(fileName, relativeTo);
-		if (!directory) {
-			return file;
+		if (suffix) {
+			if (truncateTo != null && file.length + suffix.length >= truncateTo) {
+				return `${Strings.truncateMiddle(file, truncateTo - suffix.length)}${suffix}`;
+			}
+
+			file += suffix;
+		}
+
+		return file;
+	}
+
+	static getFormattedPath(
+		fileNameOrUri: string | Uri,
+		options: {
+			relativeTo?: string;
+			suffix?: string;
+			truncateTo?: number;
+		},
+	): string {
+		const { relativeTo, suffix = emptyStr, truncateTo } = options;
+
+		let fileName: string;
+		if (fileNameOrUri instanceof Uri) {
+			fileName = fileNameOrUri.fsPath;
+		} else {
+			fileName = fileNameOrUri;
+		}
+
+		let file = paths.basename(fileName);
+		if (truncateTo != null && file.length >= truncateTo) {
+			return Strings.truncateMiddle(file, truncateTo);
 		}
 
-		if (truncateTo != null) {
-			const dirTruncateTo = truncateTo - (file.length + separator.length);
-			if (directory.length > dirTruncateTo) {
-				directory = Strings.truncateMiddle(directory, dirTruncateTo);
+		if (suffix) {
+			if (truncateTo != null && file.length + suffix.length >= truncateTo) {
+				return `${Strings.truncateMiddle(file, truncateTo - suffix.length)}${suffix}`;
 			}
+
+			file += suffix;
+		}
+
+		const directory = GitUri.getDirectory(fileName, relativeTo);
+		if (!directory) return file;
+
+		file = `/${file}`;
+
+		if (truncateTo != null && file.length + directory.length >= truncateTo) {
+			return `${Strings.truncateLeft(directory, truncateTo - file.length)}${file}`;
 		}
 
-		return `${file}${separator}${directory}`;
+		return `${directory}${file}`;
 	}
 
 	static relativeTo(fileNameOrUri: string | Uri, relativeTo: string | undefined): string {
diff --git a/src/git/models/commit.ts b/src/git/models/commit.ts
index 55d6e15..144fbfb 100644
--- a/src/git/models/commit.ts
+++ b/src/git/models/commit.ts
@@ -213,9 +213,7 @@ export abstract class GitCommit implements GitRevisionReference {
 		return this.dateFormatter.fromNow();
 	}
 
-	getFormattedPath(
-		options: { relativeTo?: string; separator?: string; suffix?: string; truncateTo?: number } = {},
-	): string {
+	getFormattedPath(options: { relativeTo?: string; suffix?: string; truncateTo?: number } = {}): string {
 		return GitUri.getFormattedPath(this.fileName, options);
 	}
 
diff --git a/src/git/models/file.ts b/src/git/models/file.ts
index 2708cb2..84ab58f 100644
--- a/src/git/models/file.ts
+++ b/src/git/models/file.ts
@@ -44,7 +44,7 @@ export namespace GitFile {
 
 	export function getFormattedPath(
 		file: GitFile,
-		options: { relativeTo?: string; separator?: string; suffix?: string; truncateTo?: number } = {},
+		options: { relativeTo?: string; suffix?: string; truncateTo?: number } = {},
 	): string {
 		return GitUri.getFormattedPath(file.fileName, options);
 	}
diff --git a/src/git/models/status.ts b/src/git/models/status.ts
index 044550d..79a23d7 100644
--- a/src/git/models/status.ts
+++ b/src/git/models/status.ts
@@ -241,7 +241,7 @@ export class GitStatusFile implements GitFile {
 		return GitFile.getFormattedDirectory(this, includeOriginal);
 	}
 
-	getFormattedPath(options: { relativeTo?: string; separator?: string; suffix?: string } = {}): string {
+	getFormattedPath(options: { relativeTo?: string; suffix?: string; truncateTo?: number } = {}): string {
 		return GitFile.getFormattedPath(this, options);
 	}
 
diff --git a/src/system/string.ts b/src/system/string.ts
index 8d86b33..00e6a4a 100644
--- a/src/system/string.ts
+++ b/src/system/string.ts
@@ -250,6 +250,7 @@ export namespace Strings {
 
 	export function truncate(s: string, truncateTo: number, ellipsis: string = '\u2026', width?: number) {
 		if (!s) return s;
+		if (truncateTo <= 1) return ellipsis;
 
 		width = width ?? getWidth(s);
 		if (width <= truncateTo) return s;
@@ -269,8 +270,31 @@ export namespace Strings {
 		return `${s.substring(0, chars)}${ellipsis}`;
 	}
 
+	export function truncateLeft(s: string, truncateTo: number, ellipsis: string = '\u2026', width?: number) {
+		if (!s) return s;
+		if (truncateTo <= 1) return ellipsis;
+
+		width = width ?? getWidth(s);
+		if (width <= truncateTo) return s;
+		if (width === s.length) return `${ellipsis}${s.substring(width - truncateTo)}`;
+
+		// Skip ahead to start as far as we can by assuming all the double-width characters won't be truncated
+		let chars = Math.floor(truncateTo / (width / s.length));
+		let count = getWidth(s.substring(0, chars));
+		while (count < truncateTo) {
+			count += getWidth(s[chars++]);
+		}
+
+		if (count >= truncateTo) {
+			chars--;
+		}
+
+		return `${ellipsis}${s.substring(s.length - chars)}`;
+	}
+
 	export function truncateMiddle(s: string, truncateTo: number, ellipsis: string = '\u2026') {
 		if (!s) return s;
+		if (truncateTo <= 1) return ellipsis;
 
 		const width = getWidth(s);
 		if (width <= truncateTo) return s;