diff --git a/workspaces/boost/dynamic-plugins-filesystem-reference.yaml b/workspaces/boost/dynamic-plugins-filesystem-reference.yaml
index 87bd1c63d74..474e4d72693 100644
--- a/workspaces/boost/dynamic-plugins-filesystem-reference.yaml
+++ b/workspaces/boost/dynamic-plugins-filesystem-reference.yaml
@@ -17,7 +17,7 @@ plugins:
   # Core backend plugin — required
   # -----------------------------------------------------------------------
   - package: ./dynamic-plugins/dist/red-hat-developer-hub-backstage-plugin-boost-backend-dynamic
-    disabled: false
+    enabled: true
     pluginConfig:
       boost:
         # Security mode: 'full' for production, 'development-only-no-auth' for local dev
@@ -38,8 +38,8 @@ plugins:
 
   # OGX provider: connects to a OGX Responses API endpoint
   - package: ./dynamic-plugins/dist/red-hat-developer-hub-backstage-plugin-boost-backend-module-ogx-dynamic
-    disabled: false
+    enabled: true
 
   # Kagenti provider: connects to a Kagenti multi-agent orchestrator
   - package: ./dynamic-plugins/dist/red-hat-developer-hub-backstage-plugin-boost-backend-module-kagenti-dynamic
-    disabled: true
+    enabled: false
diff --git a/workspaces/boost/dynamic-plugins-image-reference.yaml b/workspaces/boost/dynamic-plugins-image-reference.yaml
index 2c0314d55cb..19011f899aa 100644
--- a/workspaces/boost/dynamic-plugins-image-reference.yaml
+++ b/workspaces/boost/dynamic-plugins-image-reference.yaml
@@ -16,7 +16,7 @@ plugins:
   # Core backend plugin — required
   # -----------------------------------------------------------------------
   - package: oci://<registry>/backstage-plugin-boost-backend:<tag>!red-hat-developer-hub-backstage-plugin-boost-backend-dynamic
-    disabled: false
+    enabled: true
     pluginConfig:
       boost:
         # Security mode: 'full' for production, 'development-only-no-auth' for local dev
@@ -37,8 +37,8 @@ plugins:
 
   # OGX provider: connects to a OGX Responses API endpoint
   - package: oci://<registry>/backstage-plugin-boost-backend-module-ogx:<tag>!red-hat-developer-hub-backstage-plugin-boost-backend-module-ogx-dynamic
-    disabled: false
+    enabled: true
 
   # Kagenti provider: connects to a Kagenti multi-agent orchestrator
   - package: oci://<registry>/backstage-plugin-boost-backend-module-kagenti:<tag>!red-hat-developer-hub-backstage-plugin-boost-backend-module-kagenti-dynamic
-    disabled: true
+    enabled: false
diff --git a/workspaces/extensions/dynamic-plugins.yaml b/workspaces/extensions/dynamic-plugins.yaml
index 713beba63db..edd51d3c2ee 100644
--- a/workspaces/extensions/dynamic-plugins.yaml
+++ b/workspaces/extensions/dynamic-plugins.yaml
@@ -1,8 +1,8 @@
 plugins:
   - package: ./dynamic-plugins/dist/red-hat-developer-hub-backstage-plugin-bulk-import-backend-dynamic
-    disabled: false
+    enabled: true
   - package: ./dynamic-plugins/dist/red-hat-developer-hub-backstage-plugin-bulk-import
-    disabled: true
+    enabled: false
     pluginConfig:
       dynamicPlugins:
         frontend:
@@ -17,7 +17,7 @@ plugins:
                   icon: bulkImportIcon
                   text: Bulk import
   - package: ./dynamic-plugins/dist/red-hat-developer-hub-backstage-plugin-extensions
-    disabled: false
+    enabled: true
     pluginConfig:
       dynamicPlugins:
         frontend:
@@ -38,9 +38,9 @@ plugins:
                   path: extensions
                   title: Catalog
   - package: ./dynamic-plugins/dist/red-hat-developer-hub-backstage-plugin-extensions-backend-dynamic
-    disabled: false
+    enabled: true
   - package: ./dynamic-plugins/dist/backstage-community-plugin-quay
-    disabled: false
+    enabled: true
     # TODO: enable
     pluginConfig:
       dynamicPlugins:
@@ -56,4 +56,4 @@ plugins:
                     anyOf:
                       - isQuayAvailable
   - package: ./dynamic-plugins/dist/backstage-community-plugin-topology
-    disabled: false
+    enabled: true
diff --git a/workspaces/global-header/docs/configuration.md b/workspaces/global-header/docs/configuration.md
index f75f31d165c..1b4b3dc9ce0 100644
--- a/workspaces/global-header/docs/configuration.md
+++ b/workspaces/global-header/docs/configuration.md
@@ -24,7 +24,7 @@ The RHDH Global Header can be disabled competely by disabling the right plugin:
 ```yaml
 # Disabling global header
 - package: ./dynamic-plugins/dist/red-hat-developer-hub-backstage-plugin-global-header
-  disabled: true
+  enabled: false
 ```
 
 ## Replacing the Global Header with your own header
@@ -36,7 +36,7 @@ After that customers can implement and install their own header as a dynamic plu
 ```yaml
 # Custom header implementation
 - package: <npm or oci package-reference>
-  disabled: false
+  enabled: true
   pluginConfig:
     dynamicPlugins:
       frontend:
diff --git a/workspaces/install-dynamic-plugins/.changeset/quiet-plugin-warnings.md b/workspaces/install-dynamic-plugins/.changeset/quiet-plugin-warnings.md
new file mode 100644
index 00000000000..a0c06976ab5
--- /dev/null
+++ b/workspaces/install-dynamic-plugins/.changeset/quiet-plugin-warnings.md
@@ -0,0 +1,5 @@
+---
+'@red-hat-developer-hub/cli-module-install-dynamic-plugins': patch
+---
+
+Warn once per dynamic plugin entry that uses the deprecated `disabled` field, including entries filtered or overridden during installation. Preserve `enabled` precedence and existing plugin loading behavior.
diff --git a/workspaces/install-dynamic-plugins/packages/install-dynamic-plugins/src/installer-deprecation.test.ts b/workspaces/install-dynamic-plugins/packages/install-dynamic-plugins/src/installer-deprecation.test.ts
new file mode 100644
index 00000000000..3df017aecce
--- /dev/null
+++ b/workspaces/install-dynamic-plugins/packages/install-dynamic-plugins/src/installer-deprecation.test.ts
@@ -0,0 +1,103 @@
+/*
+ * Copyright Red Hat, Inc.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+import * as fs from 'node:fs/promises';
+import * as os from 'node:os';
+import * as path from 'node:path';
+import { main } from './installer';
+import { log } from './log';
+import type { PluginSpec } from './types';
+
+jest.mock('./log', () => ({ log: jest.fn() }));
+const warnings = () =>
+  (log as jest.Mock).mock.calls
+    .map(([message]: [string]) => message)
+    .filter((message: string) => message.includes('deprecated'));
+
+describe('dynamic-plugins.yaml disabled deprecation', () => {
+  let dir: string;
+  const originalCwd = process.cwd();
+  const originalCatalogIndex = process.env.CATALOG_INDEX_IMAGE;
+  const originalExtraIndexes = process.env.EXTRA_CATALOG_INDEX_IMAGES;
+
+  beforeEach(async () => {
+    dir = await fs.mkdtemp(path.join(os.tmpdir(), 'dp-deprecation-'));
+    process.chdir(dir);
+    delete process.env.CATALOG_INDEX_IMAGE;
+    delete process.env.EXTRA_CATALOG_INDEX_IMAGES;
+    jest.spyOn(process, 'exit').mockImplementation(() => undefined as never);
+    jest.clearAllMocks();
+  });
+
+  afterEach(async () => {
+    process.chdir(originalCwd);
+    if (originalCatalogIndex === undefined)
+      delete process.env.CATALOG_INDEX_IMAGE;
+    else process.env.CATALOG_INDEX_IMAGE = originalCatalogIndex;
+    if (originalExtraIndexes === undefined)
+      delete process.env.EXTRA_CATALOG_INDEX_IMAGES;
+    else process.env.EXTRA_CATALOG_INDEX_IMAGES = originalExtraIndexes;
+    jest.restoreAllMocks();
+    await fs.rm(dir, { recursive: true, force: true });
+  });
+
+  it('warns once per raw entry, including an overridden include and a filtered OCI entry', async () => {
+    const included: PluginSpec[] = [
+      { package: './overridden-local', disabled: true },
+      { package: 'oci://example.com/unused:1!plugin', disabled: true },
+    ];
+    await fs.writeFile(
+      path.join(dir, 'included.yaml'),
+      JSON.stringify({ plugins: included }),
+    );
+    const plugins: PluginSpec[] = [
+      { package: './overridden-local', enabled: true },
+      { package: './disabled-false-local', disabled: false },
+      { package: './both-local', enabled: false, disabled: false },
+      { package: './enabled-only-local', enabled: false },
+      { package: './neither-local' },
+    ];
+    await fs.writeFile(
+      path.join(dir, 'dynamic-plugins.yaml'),
+      JSON.stringify({ includes: ['included.yaml'], plugins }),
+    );
+    // Missing local paths skip installation, so this exercises startup without
+    // npm, OCI downloads, or a live registry.
+    await main([path.join(dir, 'dynamic-plugins-root')]);
+    expect(process.exit).toHaveBeenCalledWith(0);
+
+    expect(warnings()).toHaveLength(4);
+    expect(
+      warnings().filter(message => message.includes('./overridden-local')),
+    ).toHaveLength(1);
+    expect(
+      warnings().filter(message =>
+        message.includes('oci://example.com/unused:1!plugin'),
+      ),
+    ).toHaveLength(1);
+    expect(
+      warnings().filter(message => message.includes('./disabled-false-local')),
+    ).toHaveLength(1);
+    expect(
+      warnings().filter(message => message.includes('./both-local')),
+    ).toHaveLength(1);
+    expect(
+      warnings().some(message => message.includes('./enabled-only-local')),
+    ).toBe(false);
+    expect(
+      warnings().some(message => message.includes('./neither-local')),
+    ).toBe(false);
+  });
+});
diff --git a/workspaces/install-dynamic-plugins/packages/install-dynamic-plugins/src/installer.ts b/workspaces/install-dynamic-plugins/packages/install-dynamic-plugins/src/installer.ts
index bba28c9f352..6bf3b4f167e 100644
--- a/workspaces/install-dynamic-plugins/packages/install-dynamic-plugins/src/installer.ts
+++ b/workspaces/install-dynamic-plugins/packages/install-dynamic-plugins/src/installer.ts
@@ -333,6 +333,18 @@ export function resolveInheritPlugins(
   }
 }
 
+function warnAboutDeprecatedDisabledKeys(
+  includeLists: IncludePluginList[],
+  mainPlugins: PluginSpec[],
+): void {
+  // Warn once per declared entry, including disabled OCI entries removed by
+  // the pre-merge filter and included entries overridden by the main config.
+  for (const [, plugins] of includeLists) {
+    for (const plugin of plugins) isPluginDisabled(plugin, log);
+  }
+  for (const plugin of mainPlugins) isPluginDisabled(plugin, log);
+}
+
 /** Resolve include paths, substitute the catalog-index placeholder, merge
  * everything into a single `PluginMap`, and compute change-detection hashes.
  *
@@ -380,6 +392,8 @@ async function loadAllPlugins(
   }
   const mainPlugins = content.plugins ?? [];
 
+  warnAboutDeprecatedDisabledKeys(includeLists, mainPlugins);
+
   resolveRefPlugins(mainPlugins, includeLists);
   // Collision validation must use the packages the user declared. Resolving
   // an inherit reference replaces its requested registry with the catalog's
@@ -486,7 +500,7 @@ function categorize(allPlugins: PluginMap): Categorized {
   const npm: Plugin[] = [];
   const skipped: Plugin[] = [];
   for (const plugin of Object.values(allPlugins)) {
-    if (isPluginDisabled(plugin, log)) {
+    if (isPluginDisabled(plugin)) {
       log(`\n======= Skipping disabled plugin ${plugin.package}`);
       continue;
     }
diff --git a/workspaces/install-dynamic-plugins/packages/install-dynamic-plugins/src/types.test.ts b/workspaces/install-dynamic-plugins/packages/install-dynamic-plugins/src/types.test.ts
index b0da589c58a..686de366b1d 100644
--- a/workspaces/install-dynamic-plugins/packages/install-dynamic-plugins/src/types.test.ts
+++ b/workspaces/install-dynamic-plugins/packages/install-dynamic-plugins/src/types.test.ts
@@ -60,15 +60,35 @@ describe('isPluginDisabled', () => {
     expect(isPluginDisabled({ package: 'pkg@1.0', enabled: false })).toBe(true);
   });
 
-  it('returns true when disabled: true (backward compat)', () => {
-    expect(isPluginDisabled({ package: 'pkg@1.0', disabled: true })).toBe(true);
-  });
-
-  it('returns false when disabled: false (backward compat)', () => {
-    expect(isPluginDisabled({ package: 'pkg@1.0', disabled: false })).toBe(
-      false,
-    );
-  });
+  it.each([
+    { disabled: true, expected: true, replacement: 'enabled: false' },
+    { disabled: false, expected: false, replacement: 'enabled: true' },
+  ])(
+    'preserves disabled: $disabled and warns once',
+    ({ disabled, expected, replacement }) => {
+      const warnings: string[] = [];
+      expect(
+        isPluginDisabled({ package: 'pkg@1.0', disabled }, msg =>
+          warnings.push(msg),
+        ),
+      ).toBe(expected);
+      expect(warnings).toHaveLength(1);
+      expect(warnings[0]).toContain('Plugin pkg@1.0');
+      expect(warnings[0]).toContain(`deprecated 'disabled: ${disabled}'`);
+      expect(warnings[0]).toContain(replacement);
+    },
+  );
+
+  it.each([{ enabled: true }, { enabled: false }, {}])(
+    'does not warn without disabled: %p',
+    fields => {
+      const warnings: string[] = [];
+      isPluginDisabled({ package: 'pkg@1.0', ...fields }, msg =>
+        warnings.push(msg),
+      );
+      expect(warnings).toEqual([]);
+    },
+  );
 
   it('enabled takes precedence over disabled when both set (enabled: true, disabled: true)', () => {
     const warnings: string[] = [];
@@ -78,7 +98,12 @@ describe('isPluginDisabled', () => {
     );
     expect(result).toBe(false);
     expect(warnings).toHaveLength(1);
-    expect(warnings[0]).toMatch(/both 'enabled' and 'disabled'/);
+    expect(warnings[0]).toContain("deprecated 'disabled: true'");
+    expect(warnings[0]).toContain("new 'enabled: true'");
+    expect(warnings[0]).toContain(
+      "Remove deprecated 'disabled' in favour of preferred 'enabled' syntax.",
+    );
+    expect(warnings[0]).not.toContain('Replace it with');
   });
 
   it('enabled takes precedence over disabled when both set (enabled: false, disabled: false)', () => {
@@ -89,6 +114,12 @@ describe('isPluginDisabled', () => {
     );
     expect(result).toBe(true);
     expect(warnings).toHaveLength(1);
+    expect(warnings[0]).toContain("deprecated 'disabled: false'");
+    expect(warnings[0]).toContain("new 'enabled: false'");
+    expect(warnings[0]).toContain(
+      "Remove deprecated 'disabled' in favour of preferred 'enabled' syntax.",
+    );
+    expect(warnings[0]).not.toContain('Replace it with');
   });
 
   it('does not warn when no callback provided', () => {
@@ -141,7 +172,8 @@ describe('isPluginDisabled', () => {
       msg => warnings.push(msg),
     );
     expect(result).toBe(true);
-    expect(warnings).toHaveLength(1);
+    expect(warnings).toHaveLength(2);
     expect(warnings[0]).toMatch(/non-boolean 'enabled/);
+    expect(warnings[1]).toContain('enabled: false');
   });
 });
diff --git a/workspaces/install-dynamic-plugins/packages/install-dynamic-plugins/src/types.ts b/workspaces/install-dynamic-plugins/packages/install-dynamic-plugins/src/types.ts
index 81ee2c37599..d04a2970f26 100644
--- a/workspaces/install-dynamic-plugins/packages/install-dynamic-plugins/src/types.ts
+++ b/workspaces/install-dynamic-plugins/packages/install-dynamic-plugins/src/types.ts
@@ -31,7 +31,7 @@ export type PullPolicy = (typeof PullPolicy)[keyof typeof PullPolicy];
 export type PluginSpec = {
   package: string;
   /**
-   * Recommended: Use `enabled` instead.
+   * @deprecated Use `enabled` instead (`enabled: !disabled`).
    * When both `enabled` and `disabled` are present, `enabled` takes precedence.
    */
   disabled?: boolean;
@@ -133,10 +133,12 @@ export function effectivePullPolicy(plugin: {
  *
  *  1. When only `enabled` is set  → `disabled = !enabled`.
  *  2. When only `disabled` is set → use it directly (backward compat).
- *  3. When both are set           → `enabled` wins and a warning is emitted
- *     via the optional `warn` callback.
+ *  3. When both are set           → `enabled` wins.
  *  4. When neither is set         → default to `false` (not disabled).
  *
+ * An explicit boolean `disabled` produces one deprecation warning through
+ * the optional `warn` callback, including when `enabled` is also set.
+ *
  * Non-boolean values (e.g. the quoted string `enabled: 'false'` or
  * `enabled: null`) are treated as unset and a warning is emitted,
  * preventing JS truthiness from silently flipping activation state.
@@ -164,12 +166,16 @@ export function isPluginDisabled(
     );
   }
 
-  if (hasEnabled && hasDisabled) {
-    warn?.(
-      `WARNING: Plugin ${plugin.package} specifies both 'enabled' and 'disabled'. ` +
-        `The 'enabled' field takes precedence; please use only 'enabled'.`,
-    );
-    return !plugin.enabled;
+  if (hasDisabled) {
+    if (hasEnabled) {
+      warn?.(
+        `WARNING: Plugin ${plugin.package} uses BOTH deprecated 'disabled: ${plugin.disabled}' and new 'enabled: ${plugin.enabled}'. Remove deprecated 'disabled' in favour of preferred 'enabled' syntax.`,
+      );
+    } else {
+      warn?.(
+        `WARNING: Plugin ${plugin.package} uses deprecated 'disabled: ${plugin.disabled}' syntax. Replace it with 'enabled: ${!plugin.disabled}'.`,
+      );
+    }
   }
   if (hasEnabled) return !plugin.enabled;
   if (hasDisabled) return plugin.disabled === true;
diff --git a/workspaces/intelligent-assistant/.changeset/nasty-hairs-call.md b/workspaces/intelligent-assistant/.changeset/nasty-hairs-call.md
new file mode 100644
index 00000000000..eb8748f2006
--- /dev/null
+++ b/workspaces/intelligent-assistant/.changeset/nasty-hairs-call.md
@@ -0,0 +1,5 @@
+---
+'@red-hat-developer-hub/backstage-plugin-intelligent-assistant': patch
+---
+
+Update README to use new `enabled` field when configuring plugins, as `disabled` is now deprecated
diff --git a/workspaces/intelligent-assistant/plugins/intelligent-assistant/README.md b/workspaces/intelligent-assistant/plugins/intelligent-assistant/README.md
index b1f7f5e84f4..a7b7fb00e1a 100644
--- a/workspaces/intelligent-assistant/plugins/intelligent-assistant/README.md
+++ b/workspaces/intelligent-assistant/plugins/intelligent-assistant/README.md
@@ -289,7 +289,7 @@ Enable the plugin and its extensions in your dynamic plugins configuration:
 ```yaml
 plugins:
   - package: './local-plugins/red-hat-developer-hub-backstage-plugin-intelligent-assistant'
-    disabled: false
+    enabled: true
 ```
 
 Then configure extensions in `app-config.yaml`:
@@ -323,7 +323,7 @@ OFS mode uses Scalprum for dynamic plugin loading. Legacy exports require `modul
 ```yaml
 plugins:
   - package: './local-plugins/red-hat-developer-hub-backstage-plugin-intelligent-assistant'
-    disabled: false
+    enabled: true
     pluginConfig:
       dynamicPlugins:
         frontend:
diff --git a/workspaces/orchestrator/docs/dynamic-plugin-installation.md b/workspaces/orchestrator/docs/dynamic-plugin-installation.md
index 8bd7598bed4..d27d3fe5b4d 100644
--- a/workspaces/orchestrator/docs/dynamic-plugin-installation.md
+++ b/workspaces/orchestrator/docs/dynamic-plugin-installation.md
@@ -10,7 +10,7 @@ Include the following to the RHDH dynamic plugin configuration, replace `<tag>`
 
 ```yaml
 plugins:
-  - disabled: false
+  - enabled: true
     package: oci://ghcr.io/redhat-developer/rhdh-plugin-export-overlays/red-hat-developer-hub-backstage-plugin-orchestrator:<tag>!red-hat-developer-hub-backstage-plugin-orchestrator
     pluginConfig:
       dynamicPlugins:
@@ -43,13 +43,13 @@ plugins:
                   if:
                     anyOf:
                       - IsOrchestratorCatalogTabAvailable
-  - disabled: false
+  - enabled: true
     package: oci://ghcr.io/redhat-developer/rhdh-plugin-export-overlays/red-hat-developer-hub-backstage-plugin-orchestrator-backend:<tag>!red-hat-developer-hub-backstage-plugin-orchestrator-backend
     pluginConfig:
       orchestrator:
         dataIndexService:
           url: <data index url>
-  - disabled: false
+  - enabled: true
     package: oci://ghcr.io/redhat-developer/rhdh-plugin-export-overlays/red-hat-developer-hub-backstage-plugin-orchestrator-form-widgets:<tag>!red-hat-developer-hub-backstage-plugin-orchestrator-form-widgets
     pluginConfig:
       dynamicPlugins:
@@ -57,6 +57,6 @@ plugins:
           # OFS: load BackstagePlugin from Legacy (PluginRoot is NFS after graduation)
           red-hat-developer-hub.backstage-plugin-orchestrator-form-widgets:
             pluginModule: Legacy
-  - disabled: false
+  - enabled: true
     package: oci://ghcr.io/redhat-developer/rhdh-plugin-export-overlays/red-hat-developer-hub-backstage-plugin-scaffolder-backend-module-orchestrator:<tag>!red-hat-developer-hub-backstage-plugin-scaffolder-backend-module-orchestrator
 ```