diff --git a/src/commands/copyCurrentBranch.ts b/src/commands/copyCurrentBranch.ts
index da80a8a..c912e4d 100644
--- a/src/commands/copyCurrentBranch.ts
+++ b/src/commands/copyCurrentBranch.ts
@@ -1,9 +1,10 @@
 import type { TextEditor, Uri } from 'vscode';
-import { env, window } from 'vscode';
+import { env } from 'vscode';
 import { Commands } from '../constants';
 import type { Container } from '../container';
 import { GitUri } from '../git/gitUri';
 import { Logger } from '../logger';
+import { showGenericErrorMessage } from '../messages';
 import { RepositoryPicker } from '../quickpicks/repositoryPicker';
 import { command } from '../system/command';
 import { ActiveEditorCommand, getCommandUri } from './base';
@@ -29,7 +30,7 @@ export class CopyCurrentBranchCommand extends ActiveEditorCommand {
 			}
 		} catch (ex) {
 			Logger.error(ex, 'CopyCurrentBranchCommand');
-			void window.showErrorMessage('Unable to copy current branch name. See output channel for more details');
+			void showGenericErrorMessage('Unable to copy current branch name');
 		}
 	}
 }
diff --git a/src/commands/openBranchOnRemote.ts b/src/commands/openBranchOnRemote.ts
index cd41aae..4e7b743 100644
--- a/src/commands/openBranchOnRemote.ts
+++ b/src/commands/openBranchOnRemote.ts
@@ -1,10 +1,10 @@
 import type { TextEditor, Uri } from 'vscode';
-import { window } from 'vscode';
 import { Commands } from '../constants';
 import type { Container } from '../container';
 import { GitUri } from '../git/gitUri';
 import { RemoteResourceType } from '../git/models/remoteResource';
 import { Logger } from '../logger';
+import { showGenericErrorMessage } from '../messages';
 import { CommandQuickPickItem } from '../quickpicks/items/common';
 import { ReferencePicker, ReferencesQuickPickIncludes } from '../quickpicks/referencePicker';
 import { RepositoryPicker } from '../quickpicks/repositoryPicker';
@@ -87,9 +87,7 @@ export class OpenBranchOnRemoteCommand extends ActiveEditorCommand {
 			}));
 		} catch (ex) {
 			Logger.error(ex, 'OpenBranchOnRemoteCommand');
-			void window.showErrorMessage(
-				'Unable to open branch on remote provider. See output channel for more details',
-			);
+			void showGenericErrorMessage('Unable to open branch on remote provider');
 		}
 	}
 }
diff --git a/src/commands/openBranchesOnRemote.ts b/src/commands/openBranchesOnRemote.ts
index 80341c9..aab92ec 100644
--- a/src/commands/openBranchesOnRemote.ts
+++ b/src/commands/openBranchesOnRemote.ts
@@ -1,10 +1,10 @@
 import type { TextEditor, Uri } from 'vscode';
-import { window } from 'vscode';
 import { Commands } from '../constants';
 import type { Container } from '../container';
 import { GitUri } from '../git/gitUri';
 import { RemoteResourceType } from '../git/models/remoteResource';
 import { Logger } from '../logger';
+import { showGenericErrorMessage } from '../messages';
 import { RepositoryPicker } from '../quickpicks/repositoryPicker';
 import { command, executeCommand } from '../system/command';
 import type { CommandContext } from './base';
@@ -63,9 +63,7 @@ export class OpenBranchesOnRemoteCommand extends ActiveEditorCommand {
 			}));
 		} catch (ex) {
 			Logger.error(ex, 'OpenBranchesOnRemoteCommand');
-			void window.showErrorMessage(
-				'Unable to open branches on remote provider. See output channel for more details',
-			);
+			void showGenericErrorMessage('Unable to open branches on remote provider');
 		}
 	}
 }
diff --git a/src/commands/openCommitOnRemote.ts b/src/commands/openCommitOnRemote.ts
index 9aa835d..fbed8a4 100644
--- a/src/commands/openCommitOnRemote.ts
+++ b/src/commands/openCommitOnRemote.ts
@@ -1,12 +1,11 @@
 import type { TextEditor, Uri } from 'vscode';
-import { window } from 'vscode';
 import { Commands } from '../constants';
 import type { Container } from '../container';
 import { GitUri } from '../git/gitUri';
 import { GitRevision } from '../git/models/reference';
 import { RemoteResourceType } from '../git/models/remoteResource';
 import { Logger } from '../logger';
-import { showFileNotUnderSourceControlWarningMessage } from '../messages';
+import { showFileNotUnderSourceControlWarningMessage, showGenericErrorMessage } from '../messages';
 import { RepositoryPicker } from '../quickpicks/repositoryPicker';
 import { command, executeCommand } from '../system/command';
 import type { CommandContext } from './base';
@@ -106,9 +105,7 @@ export class OpenCommitOnRemoteCommand extends ActiveEditorCommand {
 			}));
 		} catch (ex) {
 			Logger.error(ex, 'OpenCommitOnRemoteCommand');
-			void window.showErrorMessage(
-				'Unable to open commit on remote provider. See output channel for more details',
-			);
+			void showGenericErrorMessage('Unable to open commit on remote provider');
 		}
 	}
 }
diff --git a/src/commands/openComparisonOnRemote.ts b/src/commands/openComparisonOnRemote.ts
index 2fcff53..e83e7d7 100644
--- a/src/commands/openComparisonOnRemote.ts
+++ b/src/commands/openComparisonOnRemote.ts
@@ -1,8 +1,8 @@
-import { window } from 'vscode';
 import { Commands } from '../constants';
 import type { Container } from '../container';
 import { RemoteResourceType } from '../git/models/remoteResource';
 import { Logger } from '../logger';
+import { showGenericErrorMessage } from '../messages';
 import { command, executeCommand } from '../system/command';
 import { ResultsCommitsNode } from '../views/nodes/resultsCommitsNode';
 import type { CommandContext } from './base';
@@ -58,9 +58,7 @@ export class OpenComparisonOnRemoteCommand extends Command {
 			}));
 		} catch (ex) {
 			Logger.error(ex, 'OpenComparisonOnRemoteCommand');
-			void window.showErrorMessage(
-				'Unable to open comparison on remote provider. See output channel for more details',
-			);
+			void showGenericErrorMessage('Unable to open comparison on remote provider');
 		}
 	}
 }
diff --git a/src/commands/openCurrentBranchOnRemote.ts b/src/commands/openCurrentBranchOnRemote.ts
index cb44c7f..878bb26 100644
--- a/src/commands/openCurrentBranchOnRemote.ts
+++ b/src/commands/openCurrentBranchOnRemote.ts
@@ -1,10 +1,10 @@
 import type { TextEditor, Uri } from 'vscode';
-import { window } from 'vscode';
 import { Commands } from '../constants';
 import type { Container } from '../container';
 import { GitUri } from '../git/gitUri';
 import { RemoteResourceType } from '../git/models/remoteResource';
 import { Logger } from '../logger';
+import { showGenericErrorMessage } from '../messages';
 import { RepositoryPicker } from '../quickpicks/repositoryPicker';
 import { command, executeCommand } from '../system/command';
 import { ActiveEditorCommand, getCommandUri } from './base';
@@ -37,9 +37,7 @@ export class OpenCurrentBranchOnRemoteCommand extends ActiveEditorCommand {
 			}
 		} catch (ex) {
 			Logger.error(ex, 'OpenCurrentBranchOnRemoteCommand');
-			void window.showErrorMessage(
-				'Unable to open branch on remote provider. See output channel for more details',
-			);
+			void showGenericErrorMessage('Unable to open branch on remote provider');
 		}
 	}
 }
diff --git a/src/commands/openFileOnRemote.ts b/src/commands/openFileOnRemote.ts
index 28eace5..a8caf36 100644
--- a/src/commands/openFileOnRemote.ts
+++ b/src/commands/openFileOnRemote.ts
@@ -1,5 +1,5 @@
 import type { TextEditor, Uri } from 'vscode';
-import { Range, window } from 'vscode';
+import { Range } from 'vscode';
 import { UriComparer } from '../comparers';
 import { BranchSorting, TagSorting } from '../configuration';
 import { Commands, GlyphChars } from '../constants';
@@ -9,6 +9,7 @@ import { getBranchNameWithoutRemote, getRemoteNameFromBranchName } from '../git/
 import { GitRevision } from '../git/models/reference';
 import { RemoteResourceType } from '../git/models/remoteResource';
 import { Logger } from '../logger';
+import { showGenericErrorMessage } from '../messages';
 import { ReferencePicker } from '../quickpicks/referencePicker';
 import { command, executeCommand } from '../system/command';
 import { pad, splitSingle } from '../system/string';
@@ -206,7 +207,7 @@ export class OpenFileOnRemoteCommand extends ActiveEditorCommand {
 			}));
 		} catch (ex) {
 			Logger.error(ex, 'OpenFileOnRemoteCommand');
-			void window.showErrorMessage('Unable to open file on remote provider. See output channel for more details');
+			void showGenericErrorMessage('Unable to open file on remote provider');
 		}
 	}
 }
diff --git a/src/commands/openRepoOnRemote.ts b/src/commands/openRepoOnRemote.ts
index 23daaaf..59e9104 100644
--- a/src/commands/openRepoOnRemote.ts
+++ b/src/commands/openRepoOnRemote.ts
@@ -1,10 +1,10 @@
 import type { TextEditor, Uri } from 'vscode';
-import { window } from 'vscode';
 import { Commands } from '../constants';
 import type { Container } from '../container';
 import { GitUri } from '../git/gitUri';
 import { RemoteResourceType } from '../git/models/remoteResource';
 import { Logger } from '../logger';
+import { showGenericErrorMessage } from '../messages';
 import { RepositoryPicker } from '../quickpicks/repositoryPicker';
 import { command, executeCommand } from '../system/command';
 import type { CommandContext } from './base';
@@ -61,9 +61,7 @@ export class OpenRepoOnRemoteCommand extends ActiveEditorCommand {
 			}));
 		} catch (ex) {
 			Logger.error(ex, 'OpenRepoOnRemoteCommand');
-			void window.showErrorMessage(
-				'Unable to open repository on remote provider. See output channel for more details',
-			);
+			void showGenericErrorMessage('Unable to open repository on remote provider');
 		}
 	}
 }
diff --git a/src/commands/showQuickCommitFile.ts b/src/commands/showQuickCommitFile.ts
index 7e0493b..fbf3def 100644
--- a/src/commands/showQuickCommitFile.ts
+++ b/src/commands/showQuickCommitFile.ts
@@ -1,5 +1,5 @@
 import type { TextEditor } from 'vscode';
-import { Uri, window } from 'vscode';
+import { Uri } from 'vscode';
 import { Commands } from '../constants';
 import type { Container } from '../container';
 import { GitUri } from '../git/gitUri';
@@ -100,7 +100,7 @@ export class ShowQuickCommitFileCommand extends ActiveEditorCachedCommand {
 				args.commit = blame.commit;
 			} catch (ex) {
 				Logger.error(ex, 'ShowQuickCommitFileDetailsCommand', `getBlameForLine(${blameLine})`);
-				void window.showErrorMessage('Unable to show commit file details. See output channel for more details');
+				void showGenericErrorMessage('Unable to show commit file details');
 
 				return;
 			}
diff --git a/src/commands/toggleFileAnnotations.ts b/src/commands/toggleFileAnnotations.ts
index 0139c30..0c583b8 100644
--- a/src/commands/toggleFileAnnotations.ts
+++ b/src/commands/toggleFileAnnotations.ts
@@ -137,8 +137,6 @@ async function toggleFileAnnotations<TArgs extends ToggleFileAnnotationCommandAr
 		));
 	} catch (ex) {
 		Logger.error(ex, 'ToggleFileAnnotationsCommand');
-		void window.showErrorMessage(
-			`Unable to toggle file ${args.type} annotations. See output channel for more details`,
-		);
+		void showGenericErrorMessage(`Unable to toggle file ${args.type} annotations`);
 	}
 }
diff --git a/src/commands/toggleLineBlame.ts b/src/commands/toggleLineBlame.ts
index b0ce423..c7c80ef 100644
--- a/src/commands/toggleLineBlame.ts
+++ b/src/commands/toggleLineBlame.ts
@@ -1,8 +1,8 @@
 import type { TextEditor, Uri } from 'vscode';
-import { window } from 'vscode';
 import { Commands } from '../constants';
 import type { Container } from '../container';
 import { Logger } from '../logger';
+import { showGenericErrorMessage } from '../messages';
 import { command } from '../system/command';
 import { ActiveEditorCommand } from './base';
 
@@ -17,9 +17,7 @@ export class ToggleLineBlameCommand extends ActiveEditorCommand {
 			await this.container.lineAnnotations.toggle(editor);
 		} catch (ex) {
 			Logger.error(ex, 'ToggleLineBlameCommand');
-			void window.showErrorMessage(
-				'Unable to toggle line blame annotations. See output channel for more details',
-			);
+			void showGenericErrorMessage('Unable to toggle line blame annotations');
 		}
 	}
 }
diff --git a/src/messages.ts b/src/messages.ts
index 2132734..42539d6 100644
--- a/src/messages.ts
+++ b/src/messages.ts
@@ -1,8 +1,10 @@
 import type { MessageItem } from 'vscode';
 import { ConfigurationTarget, env, Uri, window } from 'vscode';
 import { configuration, SuppressedMessages } from './configuration';
+import { Commands } from './constants';
 import type { GitCommit } from './git/models/commit';
-import { Logger } from './logger';
+import { Logger, LogLevel } from './logger';
+import { executeCommand } from './system/command';
 
 export function showCommitHasNoPreviousCommitWarningMessage(commit?: GitCommit): Promise<MessageItem | undefined> {
 	if (commit == null) {
@@ -44,20 +46,30 @@ export async function showDebugLoggingWarningMessage(): Promise<boolean> {
 	return result === disable;
 }
 
-export async function showGenericErrorMessage(message: string): Promise<MessageItem | undefined> {
-	const actions: MessageItem[] = [{ title: 'Open Output Channel' }];
-	const result = await showMessage(
-		'error',
-		`${message}. See output channel for more details`,
-		undefined,
-		null,
-		...actions,
-	);
+export async function showGenericErrorMessage(message: string): Promise<void> {
+	if (Logger.enabled(LogLevel.Error)) {
+		const result = await showMessage('error', `${message}. See output channel for more details.`, undefined, null, {
+			title: 'Open Output Channel',
+		});
 
-	if (result !== undefined) {
-		Logger.showOutputChannel();
+		if (result != null) {
+			Logger.showOutputChannel();
+		}
+	} else {
+		const result = await showMessage(
+			'error',
+			`${message}. If the error persists, please enable debug logging and try again.`,
+			undefined,
+			null,
+			{
+				title: 'Enable Debug Logging',
+			},
+		);
+
+		if (result != null) {
+			void executeCommand(Commands.EnableDebugLogging);
+		}
 	}
-	return result;
 }
 
 export function showFileNotUnderSourceControlWarningMessage(message: string): Promise<MessageItem | undefined> {