diff --git a/CHANGELOG.md b/CHANGELOG.md
index 37689bb96ee67..4a3e48df83c6c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,11 +5,13 @@
 - [Previous Changelogs](https://github.com/eclipse-theia/theia/tree/master/doc/changelogs/)
 
 
-## v1.38.0 - 04/27/2023
+## v1.38.0 - 05/25/2023
 
 <a name="breaking_changes_1.38.0">[Breaking Changes:](#breaking_changes_1.38.0)</a>
 
 - [core] moved `ToolbarAwareTabBar.Styles` to `ScrollableTabBar.Styles` [12411](https://github.com/eclipse-theia/theia/pull/12411/)
+- [debug] Change the return type of (method) `DebugConfigurationManager.provideDynamicDebugConfigurations()` to <br>
+`Promise<Record<string, DynamicDebugConfigurationSessionOptions[]>>` [#12482](https://github.com/eclipse-theia/theia/pull/12482)
 
 ## v1.37.0 - 04/27/2023
 
diff --git a/packages/debug/src/browser/debug-configuration-manager.ts b/packages/debug/src/browser/debug-configuration-manager.ts
index c4996ba79318e..d9ee87e0756ff 100644
--- a/packages/debug/src/browser/debug-configuration-manager.ts
+++ b/packages/debug/src/browser/debug-configuration-manager.ts
@@ -178,8 +178,8 @@ export class DebugConfigurationManager {
 
         // Refresh a dynamic configuration from the provider.
         // This allow providers to update properties before the execution e.g. program
-        const { providerType, configuration: { name } } = this._currentOptions;
-        const configuration = await this.fetchDynamicDebugConfiguration(name, providerType);
+        const { providerType, workspaceFolderUri, configuration: { name } } = this._currentOptions;
+        const configuration = await this.fetchDynamicDebugConfiguration(name, providerType, workspaceFolderUri);
 
         if (!configuration) {
             const message = nls.localize(
@@ -188,7 +188,7 @@ export class DebugConfigurationManager {
             throw new Error(message);
         }
 
-        return { name, configuration, providerType };
+        return { name, configuration, providerType, workspaceFolderUri };
     }
 
     set current(option: DebugSessionOptions | undefined) {
@@ -215,7 +215,8 @@ export class DebugConfigurationManager {
     protected dynamicOptionsMatch(one: DynamicDebugConfigurationSessionOptions, other: DynamicDebugConfigurationSessionOptions): boolean {
         return one.providerType !== undefined
             && one.configuration.name === other.configuration.name
-            && one.providerType === other.providerType;
+            && one.providerType === other.providerType
+            && one.workspaceFolderUri === other.workspaceFolderUri;
     }
 
     get recentDynamicOptions(): readonly DynamicDebugConfigurationSessionOptions[] {
@@ -462,14 +463,40 @@ export class DebugConfigurationManager {
         await WaitUntilEvent.fire(this.onWillProvideDebugConfigurationEmitter, {});
     }
 
-    async provideDynamicDebugConfigurations(): Promise<Record<string, DebugConfiguration[]>> {
+    async provideDynamicDebugConfigurations(): Promise<Record<string, DynamicDebugConfigurationSessionOptions[]>> {
         await this.fireWillProvideDynamicDebugConfiguration();
-        return this.debug.provideDynamicDebugConfigurations!();
+        const roots = this.workspaceService.tryGetRoots();
+        const promises = roots.map(async root => {
+            const configsMap = await this.debug.provideDynamicDebugConfigurations!(root.resource.toString());
+            const optionsMap = Object.fromEntries(Object.entries(configsMap).map(([type, configs]) => {
+                const options = configs.map(config => ({
+                    name: config.name,
+                    providerType: type,
+                    configuration: config,
+                    workspaceFolderUri: root.resource.toString()
+                }));
+                return [type, options];
+            }));
+            return optionsMap;
+        });
+
+        const typesToOptionsRecords = await Promise.all(promises);
+        const consolidatedTypesToOptions: Record<string, DynamicDebugConfigurationSessionOptions[]> = {};
+
+        for (const typesToOptionsInstance of typesToOptionsRecords) {
+            for (const [providerType, configurationsOptions] of Object.entries(typesToOptionsInstance)) {
+                if (!consolidatedTypesToOptions[providerType]) {
+                    consolidatedTypesToOptions[providerType] = [];
+                }
+                consolidatedTypesToOptions[providerType].push(...configurationsOptions);
+            }
+        }
+        return consolidatedTypesToOptions;
     }
 
-    async fetchDynamicDebugConfiguration(name: string, type: string): Promise<DebugConfiguration | undefined> {
+    async fetchDynamicDebugConfiguration(name: string, type: string, folder?: string): Promise<DebugConfiguration | undefined> {
         await this.fireWillProvideDynamicDebugConfiguration();
-        return this.debug.fetchDynamicDebugConfiguration(name, type);
+        return this.debug.fetchDynamicDebugConfiguration(name, type, folder);
     }
 
     protected async fireWillProvideDynamicDebugConfiguration(): Promise<void> {
diff --git a/packages/debug/src/browser/debug-prefix-configuration.ts b/packages/debug/src/browser/debug-prefix-configuration.ts
index 70bbcc6330f2e..613b5c4d71c47 100644
--- a/packages/debug/src/browser/debug-prefix-configuration.ts
+++ b/packages/debug/src/browser/debug-prefix-configuration.ts
@@ -107,6 +107,12 @@ export class DebugPrefixConfiguration implements CommandContribution, CommandHan
         });
     }
 
+    protected resolveRootFolderName(uri: string | undefined): string | undefined {
+        return uri && this.workspaceService.isMultiRootWorkspaceOpened
+            ? this.labelProvider.getName(new URI(uri))
+            : '';
+    }
+
     async getPicks(filter: string, token: CancellationToken): Promise<QuickPicks> {
         const items: QuickPickItemOrSeparator[] = [];
         const configurations = this.debugConfigurationManager.all;
@@ -114,27 +120,26 @@ export class DebugPrefixConfiguration implements CommandContribution, CommandHan
         for (const config of configurations) {
             items.push({
                 label: config.name,
-                description: this.workspaceService.isMultiRootWorkspaceOpened
-                    ? this.labelProvider.getName(new URI(config.workspaceFolderUri))
-                    : '',
+                description: this.resolveRootFolderName(config.workspaceFolderUri),
                 execute: () => this.runConfiguration(config)
             });
         }
 
         // Resolve dynamic configurations from providers
         const record = await this.debugConfigurationManager.provideDynamicDebugConfigurations();
-        for (const [providerType, dynamicConfigurations] of Object.entries(record)) {
-            if (dynamicConfigurations.length > 0) {
+        for (const [providerType, configurationOptions] of Object.entries(record)) {
+            if (configurationOptions.length > 0) {
                 items.push({
                     label: providerType,
                     type: 'separator'
                 });
             }
 
-            for (const configuration of dynamicConfigurations) {
+            for (const options of configurationOptions) {
                 items.push({
-                    label: configuration.name,
-                    execute: () => this.runConfiguration({ name: configuration.name, configuration, providerType })
+                    label: options.name,
+                    description: this.resolveRootFolderName(options.workspaceFolderUri),
+                    execute: () => this.runConfiguration({ name: options.name, configuration: options.configuration, providerType, workspaceFolderUri: options.workspaceFolderUri })
                 });
             }
         }
diff --git a/packages/debug/src/browser/view/debug-configuration-select.tsx b/packages/debug/src/browser/view/debug-configuration-select.tsx
index 091ef1b3b31e4..7e3f1537128ec 100644
--- a/packages/debug/src/browser/view/debug-configuration-select.tsx
+++ b/packages/debug/src/browser/view/debug-configuration-select.tsx
@@ -22,7 +22,7 @@ import { SelectComponent, SelectOption } from '@theia/core/lib/browser/widgets/s
 import { QuickInputService } from '@theia/core/lib/browser';
 import { nls } from '@theia/core/lib/common/nls';
 
-interface DynamicPickItem { label: string, configurationType: string, request: string, providerType: string }
+interface DynamicPickItem { label: string, configurationType: string, request: string, providerType: string, workspaceFolderUri?: string }
 
 export interface DebugConfigurationSelectProps {
     manager: DebugConfigurationManager,
@@ -130,11 +130,13 @@ export class DebugConfigurationSelect extends React.Component<DebugConfiguration
             return [];
         }
 
-        return configurationsOfProviderType.map(configuration => ({
-            label: configuration.name,
-            configurationType: configuration.type,
-            request: configuration.request,
-            providerType
+        return configurationsOfProviderType.map(options => ({
+            label: options.configuration.name,
+            configurationType: options.configuration.type,
+            request: options.configuration.request,
+            providerType: options.providerType,
+            description: this.toBaseName(options.workspaceFolderUri),
+            workspaceFolderUri: options.workspaceFolderUri
         }));
     }
 
@@ -161,15 +163,15 @@ export class DebugConfigurationSelect extends React.Component<DebugConfiguration
             type: selected.configurationType,
             request: selected.request
         };
-        this.manager.current = this.manager.find(selectedConfiguration, undefined, selected.providerType);
+        this.manager.current = this.manager.find(selectedConfiguration, selected.workspaceFolderUri, selected.providerType);
         this.refreshDebugConfigurations();
     }
 
     protected refreshDebugConfigurations = async () => {
-        const configsPerType = await this.manager.provideDynamicDebugConfigurations();
+        const configsOptionsPerType = await this.manager.provideDynamicDebugConfigurations();
         const providerTypes = [];
-        for (const [type, configurations] of Object.entries(configsPerType)) {
-            if (configurations.length > 0) {
+        for (const [type, configurationsOptions] of Object.entries(configsOptionsPerType)) {
+            if (configurationsOptions.length > 0) {
                 providerTypes.push(type);
             }
         }
@@ -251,6 +253,10 @@ export class DebugConfigurationSelect extends React.Component<DebugConfiguration
         if (!options.workspaceFolderUri || !multiRoot) {
             return name;
         }
-        return `${name} (${new URI(options.workspaceFolderUri).path.base})`;
+        return `${name} (${this.toBaseName(options.workspaceFolderUri)})`;
+    }
+
+    protected toBaseName(uri: string | undefined): string {
+        return uri ? new URI(uri).path.base : '';
     }
 }
diff --git a/packages/debug/src/common/debug-service.ts b/packages/debug/src/common/debug-service.ts
index 67ee916e90968..52077893316ac 100644
--- a/packages/debug/src/common/debug-service.ts
+++ b/packages/debug/src/common/debug-service.ts
@@ -80,12 +80,12 @@ export interface DebugService extends Disposable {
     /**
      * @returns A Record of debug configuration provider types and a corresponding dynamic debug configurations array
      */
-    provideDynamicDebugConfigurations?(): Promise<Record<string, DebugConfiguration[]>>;
+    provideDynamicDebugConfigurations?(folder?: string): Promise<Record<string, DebugConfiguration[]>>;
 
     /**
      * Provides a dynamic debug configuration matching the name and the provider debug type
      */
-    fetchDynamicDebugConfiguration(name: string, type: string): Promise<DebugConfiguration | undefined>;
+    fetchDynamicDebugConfiguration(name: string, type: string, folder?: string): Promise<DebugConfiguration | undefined>;
 
     /**
      * Resolves a [debug configuration](#DebugConfiguration) by filling in missing values
diff --git a/packages/debug/src/node/debug-service-impl.ts b/packages/debug/src/node/debug-service-impl.ts
index c4304390b1947..f5e1e6aa1e054 100644
--- a/packages/debug/src/node/debug-service-impl.ts
+++ b/packages/debug/src/node/debug-service-impl.ts
@@ -71,7 +71,7 @@ export class DebugServiceImpl implements DebugService {
         // TODO: Support dynamic debug configurations through Theia extensions?
         return {};
     }
-    fetchDynamicDebugConfiguration(name: string, type: string): Promise<DebugConfiguration | undefined> {
+    fetchDynamicDebugConfiguration(name: string, type: string, folder?: string): Promise<DebugConfiguration | undefined> {
         // TODO: Support dynamic debug configurations through Theia extensions?
         return Promise.resolve(undefined);
     }
diff --git a/packages/plugin-ext/src/main/browser/debug/plugin-debug-service.ts b/packages/plugin-ext/src/main/browser/debug/plugin-debug-service.ts
index 1e7576edeab2a..ecb575c109200 100644
--- a/packages/plugin-ext/src/main/browser/debug/plugin-debug-service.ts
+++ b/packages/plugin-ext/src/main/browser/debug/plugin-debug-service.ts
@@ -142,7 +142,7 @@ export class PluginDebugService implements DebugService {
         return results;
     }
 
-    async fetchDynamicDebugConfiguration(name: string, providerType: string): Promise<DebugConfiguration | undefined> {
+    async fetchDynamicDebugConfiguration(name: string, providerType: string, folder?: string): Promise<DebugConfiguration | undefined> {
         const pluginProviders =
             Array.from(this.configurationProviders.values()).filter(p => (
                 p.triggerKind === DebugConfigurationProviderTriggerKind.Dynamic &&
@@ -151,7 +151,7 @@ export class PluginDebugService implements DebugService {
             ));
 
         for (const provider of pluginProviders) {
-            const configurations = await provider.provideDebugConfigurations(undefined);
+            const configurations = await provider.provideDebugConfigurations(folder);
             for (const configuration of configurations) {
                 if (configuration.name === name) {
                     return configuration;
@@ -160,7 +160,7 @@ export class PluginDebugService implements DebugService {
         }
     }
 
-    async provideDynamicDebugConfigurations(): Promise<Record<string, DebugConfiguration[]>> {
+    async provideDynamicDebugConfigurations(folder?: string): Promise<Record<string, DebugConfiguration[]>> {
         const pluginProviders =
             Array.from(this.configurationProviders.values()).filter(p => (
                 p.triggerKind === DebugConfigurationProviderTriggerKind.Dynamic &&
@@ -170,7 +170,7 @@ export class PluginDebugService implements DebugService {
         const configurationsRecord: Record<string, DebugConfiguration[]> = {};
 
         await Promise.all(pluginProviders.map(async provider => {
-            const configurations = await provider.provideDebugConfigurations(undefined);
+            const configurations = await provider.provideDebugConfigurations(folder);
             let configurationsPerType = configurationsRecord[provider.type];
             configurationsPerType = configurationsPerType ? configurationsPerType.concat(configurations) : configurations;