diff --git a/CHANGELOG.md b/CHANGELOG.md
index 17f4f03b657be..9fd93ec74f92e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -20,6 +20,7 @@ The format is based on [Keep a Changelog](http://keepachangelog.com/) and this p
 - Adds _Open Comparison on Remote_ command to branch comparisons in views
 - Adds _Open in Worktree_ context menu command to branches and pull requests in views and the _Commit Graph_
 - Adds an option to delete a worktree along with its branch from the _Git Delete Worktree_ command
+- Adds a step to delete the worktree of a branch first if one exists when using the _Git Delete Branch_ command
 
 ### Changed
 
diff --git a/src/commands/git/branch.ts b/src/commands/git/branch.ts
index eb5b1154cfc1c..3004c3bdcb12d 100644
--- a/src/commands/git/branch.ts
+++ b/src/commands/git/branch.ts
@@ -3,6 +3,7 @@ import type { Container } from '../../container';
 import type { GitBranchReference, GitReference } from '../../git/models/reference';
 import { getNameWithoutRemote, getReferenceLabel, isRevisionReference } from '../../git/models/reference';
 import { Repository } from '../../git/models/repository';
+import type { GitWorktree } from '../../git/models/worktree';
 import type { QuickPickItemOfT } from '../../quickpicks/items/common';
 import { createQuickPickSeparator } from '../../quickpicks/items/common';
 import type { FlagsQuickPickItem } from '../../quickpicks/items/flags';
@@ -422,7 +423,10 @@ export class BranchGitCommand extends QuickCommand {
 		return canPickStepContinue(step, state, selection) ? selection[0].item : StepResultBreak;
 	}
 
-	private *deleteCommandSteps(state: DeleteStepState | PruneStepState, context: Context): StepResultGenerator<void> {
+	private async *deleteCommandSteps(
+		state: DeleteStepState | PruneStepState,
+		context: Context,
+	): AsyncStepResultGenerator<void> {
 		const prune = state.subcommand === 'prune';
 		if (state.flags == null) {
 			state.flags = [];
@@ -463,6 +467,29 @@ export class BranchGitCommand extends QuickCommand {
 			);
 
 			assertStateStepDeleteBranches(state);
+
+			const worktrees = await this.getWorktreesOfSelectedBranches(state);
+			if (worktrees.length) {
+				const result = yield* getSteps(
+					this.container,
+					{
+						command: 'worktree',
+						state: {
+							subcommand: 'delete',
+							repo: state.repo,
+							uris: worktrees.map(wt => wt.uri),
+							flags: ['--deleting-of-selected-branches'],
+						},
+					},
+					this.pickedVia,
+				);
+				if (result !== StepResultBreak) {
+					// we get here if it was a step back from the delete worktrees picker
+					state.counter--;
+					continue;
+				}
+			}
+
 			const result = yield* this.deleteCommandConfirmStep(state, context);
 			if (result === StepResultBreak) continue;
 
@@ -476,6 +503,20 @@ export class BranchGitCommand extends QuickCommand {
 		}
 	}
 
+	private async getWorktreesOfSelectedBranches(state: DeleteStepState | PruneStepState): Promise<GitWorktree[]> {
+		const worktrees = await state.repo.getWorktrees();
+
+		const refs = new Set<string>(
+			Array.isArray(state.references)
+				? state.references.map(r => r.name)
+				: state.references != null
+				  ? [state.references.name]
+				  : undefined,
+		);
+
+		return worktrees.filter(wt => wt.branch && refs.has(wt.branch.name));
+	}
+
 	private *deleteCommandConfirmStep(
 		state:
 			| DeleteStepState<ExcludeSome<DeleteState, 'references', GitBranchReference>>
diff --git a/src/commands/git/worktree.ts b/src/commands/git/worktree.ts
index eb5544c8c70bb..e270678b6cfb1 100644
--- a/src/commands/git/worktree.ts
+++ b/src/commands/git/worktree.ts
@@ -103,7 +103,7 @@ interface CreateState {
 	skipWorktreeConfirmations?: boolean;
 }
 
-type DeleteFlags = '--force' | '--delete-branches';
+type DeleteFlags = '--force' | '--delete-branches' | '--deleting-of-selected-branches';
 
 interface DeleteState {
 	subcommand: 'delete';
@@ -953,7 +953,9 @@ export class WorktreeGitCommand extends QuickCommand<State> {
 	private *deleteCommandConfirmStep(state: DeleteStepState, context: Context): StepResultGenerator<DeleteFlags[]> {
 		context.title = state.uris.length === 1 ? 'Delete Worktree' : 'Delete Worktrees';
 		const label = state.uris.length === 1 ? 'Delete Worktree' : 'Delete Worktrees';
+		const deletingOfSelectedBranches = state.flags.includes('--deleting-of-selected-branches');
 		const branchesLabel = state.uris.length === 1 ? 'Branch' : 'Branches';
+		const selectedBranchesLabelSuffix = !deletingOfSelectedBranches ? '' : ` of ${branchesLabel}`;
 		const description =
 			state.uris.length === 1
 				? `delete worktree in $(folder) ${getWorkspaceFriendlyPath(state.uris[0])}`
@@ -964,23 +966,27 @@ export class WorktreeGitCommand extends QuickCommand<State> {
 			appendReposToTitle(`Confirm ${context.title}`, state, context),
 			[
 				createFlagsQuickPickItem<DeleteFlags>(state.flags, [], {
-					label: label,
+					label: `${label}${selectedBranchesLabelSuffix}`,
 					detail: `Will ${description}`,
 				}),
 				createFlagsQuickPickItem<DeleteFlags>(state.flags, ['--force'], {
-					label: `Force ${label}`,
+					label: `Force ${label}${selectedBranchesLabelSuffix}`,
 					description: 'includes ANY UNCOMMITTED changes',
 					detail: `Will forcibly ${description}`,
 				}),
-				createFlagsQuickPickItem<DeleteFlags>(state.flags, ['--delete-branches'], {
-					label: `${label} & ${branchesLabel}`,
-					detail: `Will ${description} ${branchesDescription}`,
-				}),
-				createFlagsQuickPickItem<DeleteFlags>(state.flags, ['--force', '--delete-branches'], {
-					label: `Force ${label} & ${branchesLabel}`,
-					description: 'includes ANY UNCOMMITTED changes',
-					detail: `Will forcibly ${description} ${branchesDescription}`,
-				}),
+				...(deletingOfSelectedBranches
+					? []
+					: [
+							createFlagsQuickPickItem<DeleteFlags>(state.flags, ['--delete-branches'], {
+								label: `${label} & ${branchesLabel}`,
+								detail: `Will ${description} ${branchesDescription}`,
+							}),
+							createFlagsQuickPickItem<DeleteFlags>(state.flags, ['--force', '--delete-branches'], {
+								label: `Force ${label} & ${branchesLabel}`,
+								description: 'includes ANY UNCOMMITTED changes',
+								detail: `Will forcibly ${description} ${branchesDescription}`,
+							}),
+					  ]),
 			],
 			context,
 		);