diff --git a/apps/browser/src/_locales/en/messages.json b/apps/browser/src/_locales/en/messages.json
index ce5787c46bd..996bdcdae79 100644
--- a/apps/browser/src/_locales/en/messages.json
+++ b/apps/browser/src/_locales/en/messages.json
@@ -4246,6 +4246,26 @@
   "commonImportFormats": {
     "message": "Common formats",
     "description": "Label indicating the most common import formats"
+  },
+   "uriMatchDefaultStrategyHint": {
+    "message": "URI match detection is how Bitwarden identifies autofill suggestions.",
+    "description": "Explains to the user that URI match detection determines how Bitwarden suggests autofill options, and clarifies that this default strategy applies when no specific match detection is set for a login item."  
+  },
+   "regExAdvancedOptionWarning": {
+    "message": "\"Regular expression\" is an advanced option with increased risk of exposing credentials.",
+    "description": "Content for dialog which warns a user when selecting 'regular expression' matching strategy as a cipher match strategy"
+  },
+   "startsWithAdvancedOptionWarning": {
+    "message": "\"Starts with\" is an advanced option with increased risk of exposing credentials.",
+    "description": "Content for dialog which warns a user when selecting 'starts with' matching strategy as a cipher match strategy"
+  },
+  "uriMatchWarningDialogLink": {
+    "message": "More about match detection",
+    "description": "Link to match detection docs on warning dialog for advance match strategy"
+  },
+  "uriAdvancedOption":{
+    "message": "Advanced options",
+    "description": "Advanced option placeholder for uri option component"
   },
   "confirmContinueToBrowserSettingsTitle": {
     "message": "Continue to browser settings?",
diff --git a/apps/desktop/src/locales/en/messages.json b/apps/desktop/src/locales/en/messages.json
index ac9307c482c..991d07fb9df 100644
--- a/apps/desktop/src/locales/en/messages.json
+++ b/apps/desktop/src/locales/en/messages.json
@@ -3534,6 +3534,22 @@
   "commonImportFormats": {
     "message": "Common formats",
     "description": "Label indicating the most common import formats"
+  },
+     "uriMatchDefaultStrategyHint": {
+    "message": "URI match detection is how Bitwarden identifies autofill suggestions.",
+    "description": "Explains to the user that URI match detection determines how Bitwarden suggests autofill options, and clarifies that this default strategy applies when no specific match detection is set for a login item."  
+  },
+   "regExAdvancedOptionWarning": {
+    "message": "\"Regular expression\" is an advanced option with increased risk of exposing credentials.",
+    "description": "Content for dialog which warns a user when selecting 'regular expression' matching strategy as a cipher match strategy"
+  },
+   "startsWithAdvancedOptionWarning": {
+    "message": "\"Starts with\" is an advanced option with increased risk of exposing credentials.",
+    "description": "Content for dialog which warns a user when selecting 'starts with' matching strategy as a cipher match strategy"
+  },
+  "uriMatchWarningDialogLink": {
+    "message": "More about match detection",
+    "description": "Link to match detection docs on warning dialog for advance match strategy"
   },
   "success": {
     "message": "Success"
diff --git a/apps/web/src/locales/en/messages.json b/apps/web/src/locales/en/messages.json
index 6ed8ffe9bb3..ce35f2abd33 100644
--- a/apps/web/src/locales/en/messages.json
+++ b/apps/web/src/locales/en/messages.json
@@ -8907,6 +8907,22 @@
   "commonImportFormats": {
     "message": "Common formats",
     "description": "Label indicating the most common import formats"
+  },
+     "uriMatchDefaultStrategyHint": {
+    "message": "URI match detection is how Bitwarden identifies autofill suggestions.",
+    "description": "Explains to the user that URI match detection determines how Bitwarden suggests autofill options, and clarifies that this default strategy applies when no specific match detection is set for a login item."  
+  },
+   "regExAdvancedOptionWarning": {
+    "message": "\"Regular expression\" is an advanced option with increased risk of exposing credentials.",
+    "description": "Content for dialog which warns a user when selecting 'regular expression' matching strategy as a cipher match strategy"
+  },
+   "startsWithAdvancedOptionWarning": {
+    "message": "\"Starts with\" is an advanced option with increased risk of exposing credentials.",
+    "description": "Content for dialog which warns a user when selecting 'starts with' matching strategy as a cipher match strategy"
+  },
+  "uriMatchWarningDialogLink": {
+    "message": "More about match detection",
+    "description": "Link to match detection docs on warning dialog for advance match strategy"
   },
   "maintainYourSubscription": {
     "message": "To maintain your subscription for $ORG$, ",
diff --git a/libs/vault/src/cipher-form/components/autofill-options/advanced-uri-option-dialog.component.html b/libs/vault/src/cipher-form/components/autofill-options/advanced-uri-option-dialog.component.html
new file mode 100644
index 00000000000..627989a3397
--- /dev/null
+++ b/libs/vault/src/cipher-form/components/autofill-options/advanced-uri-option-dialog.component.html
@@ -0,0 +1,27 @@
+<bit-simple-dialog>
+  <i
+    bitDialogIcon
+    class="bwi tw-text-3xl bwi-exclamation-triangle tw-text-warning"
+    aria-hidden="true"
+  ></i>
+  <span bitDialogTitle>
+    {{ "warningCapitalized" | i18n }}
+  </span>
+  <div bitDialogContent>
+    <p>
+      {{ contentKey | i18n }}
+      <br />
+      <button bitLink type="button" linkType="primary" (click)="openLink($event)">
+        {{ "uriMatchWarningDialogLink" | i18n }}
+      </button>
+    </p>
+  </div>
+  <ng-container bitDialogFooter>
+    <button bitButton type="button" buttonType="primary" (click)="onContinue()">
+      {{ "continue" | i18n }}
+    </button>
+    <button bitButton type="button" buttonType="secondary" (click)="onCancel()">
+      {{ "cancel" | i18n }}
+    </button>
+  </ng-container>
+</bit-simple-dialog>
diff --git a/libs/vault/src/cipher-form/components/autofill-options/advanced-uri-option-dialog.component.ts b/libs/vault/src/cipher-form/components/autofill-options/advanced-uri-option-dialog.component.ts
new file mode 100644
index 00000000000..e63aa224149
--- /dev/null
+++ b/libs/vault/src/cipher-form/components/autofill-options/advanced-uri-option-dialog.component.ts
@@ -0,0 +1,58 @@
+import { Component, inject } from "@angular/core";
+
+import { JslibModule } from "@bitwarden/angular/jslib.module";
+import { PlatformUtilsService } from "@bitwarden/common/platform/abstractions/platform-utils.service";
+import {
+  ButtonLinkDirective,
+  ButtonModule,
+  DialogModule,
+  DialogService,
+  DIALOG_DATA,
+  DialogRef,
+} from "@bitwarden/components";
+
+export type AdvancedUriOptionDialogParams = {
+  contentKey: string;
+  onCancel: () => void;
+  onContinue: () => void;
+};
+
+@Component({
+  templateUrl: "advanced-uri-option-dialog.component.html",
+  imports: [ButtonLinkDirective, ButtonModule, DialogModule, JslibModule],
+})
+export class AdvancedUriOptionDialogComponent {
+  constructor(private dialogRef: DialogRef<boolean>) {}
+
+  protected platformUtilsService = inject(PlatformUtilsService);
+  protected params = inject<AdvancedUriOptionDialogParams>(DIALOG_DATA);
+
+  get contentKey(): string {
+    return this.params.contentKey;
+  }
+
+  onCancel() {
+    this.params.onCancel?.();
+    this.dialogRef.close(false);
+  }
+
+  onContinue() {
+    this.params.onContinue?.();
+    this.dialogRef.close(true);
+  }
+
+  openLink(event: Event) {
+    event.preventDefault();
+    this.platformUtilsService.launchUri("https://bitwarden.com/help/uri-match-detection/");
+  }
+
+  static open(
+    dialogService: DialogService,
+    params: AdvancedUriOptionDialogParams,
+  ): DialogRef<boolean> {
+    return dialogService.open<boolean>(AdvancedUriOptionDialogComponent, {
+      data: params,
+      disableClose: true,
+    });
+  }
+}
diff --git a/libs/vault/src/cipher-form/components/autofill-options/uri-option.component.html b/libs/vault/src/cipher-form/components/autofill-options/uri-option.component.html
index 84b43edfbac..2e88a68a0d4 100644
--- a/libs/vault/src/cipher-form/components/autofill-options/uri-option.component.html
+++ b/libs/vault/src/cipher-form/components/autofill-options/uri-option.component.html
@@ -6,7 +6,7 @@
         <input bitInput formControlName="uri" #uriInput />
         <button
           type="button"
-          bitIconButton="bwi-cog"
+          [bitIconButton]="showMatchDetection ? 'bwi-cog-f' : 'bwi-cog'"
           bitSuffix
           [appA11yTitle]="toggleTitle"
           (click)="toggleMatchDetection()"
@@ -43,8 +43,16 @@
           *ngFor="let o of uriMatchOptions"
           [label]="o.label"
           [value]="o.value"
+          [disabled]="o.disabled"
         ></bit-option>
       </bit-select>
+      <bit-hint *ngIf="getMatchHints() as hints">
+        {{ hints[0] | i18n }}
+        <ng-container *ngIf="hints.length > 1">
+          <b>{{ "warningCapitalized" | i18n }}:</b>
+          {{ hints[1] | i18n }}
+        </ng-container>
+      </bit-hint>
     </bit-form-field>
   </div>
 </ng-container>
diff --git a/libs/vault/src/cipher-form/components/autofill-options/uri-option.component.spec.ts b/libs/vault/src/cipher-form/components/autofill-options/uri-option.component.spec.ts
index d259566cc57..0d7f3663967 100644
--- a/libs/vault/src/cipher-form/components/autofill-options/uri-option.component.spec.ts
+++ b/libs/vault/src/cipher-form/components/autofill-options/uri-option.component.spec.ts
@@ -1,14 +1,19 @@
 import { ComponentFixture, TestBed } from "@angular/core/testing";
 import { NG_VALUE_ACCESSOR } from "@angular/forms";
+import { of } from "rxjs";
 
 import { UriMatchStrategy } from "@bitwarden/common/models/domain/domain-service";
 import { I18nService } from "@bitwarden/common/platform/abstractions/i18n.service";
+import { DialogRef, DialogService } from "@bitwarden/components";
 
+import { AdvancedUriOptionDialogComponent } from "./advanced-uri-option-dialog.component";
 import { UriOptionComponent } from "./uri-option.component";
 
 describe("UriOptionComponent", () => {
   let component: UriOptionComponent;
   let fixture: ComponentFixture<UriOptionComponent>;
+  let dialogServiceMock: jest.Mocked<DialogService>;
+  let dialogRefMock: jest.Mocked<DialogRef<boolean>>;
 
   const getToggleMatchDetectionBtn = () =>
     fixture.nativeElement.querySelector(
@@ -26,9 +31,19 @@ describe("UriOptionComponent", () => {
     ) as HTMLButtonElement;
 
   beforeEach(async () => {
+    dialogServiceMock = {
+      open: jest.fn().mockReturnValue(dialogRefMock),
+    } as unknown as jest.Mocked<DialogService>;
+
+    dialogRefMock = {
+      close: jest.fn(),
+      afterClosed: jest.fn().mockReturnValue(of(true)),
+    } as unknown as jest.Mocked<DialogRef<boolean>>;
+
     await TestBed.configureTestingModule({
       imports: [UriOptionComponent],
       providers: [
+        { provide: DialogService, useValue: dialogServiceMock },
         {
           provide: I18nService,
           useValue: { t: (...keys: string[]) => keys.filter(Boolean).join(" ") },
@@ -165,4 +180,36 @@ describe("UriOptionComponent", () => {
       expect(component.remove.emit).toHaveBeenCalled();
     });
   });
+
+  describe("advanced match strategy dialog", () => {
+    function testDialogAction(action: "onContinue" | "onCancel", expected: number) {
+      const openSpy = jest
+        .spyOn(AdvancedUriOptionDialogComponent, "open")
+        .mockReturnValue(dialogRefMock);
+
+      component["uriForm"].controls.matchDetection.setValue(UriMatchStrategy.Domain);
+      component["uriForm"].controls.matchDetection.setValue(UriMatchStrategy.StartsWith);
+
+      const [, params] = openSpy.mock.calls[0] as [
+        DialogService,
+        {
+          contentKey: string;
+          onContinue: () => void;
+          onCancel: () => void;
+        },
+      ];
+
+      params[action]();
+
+      expect(component["uriForm"].value.matchDetection).toBe(expected);
+    }
+
+    it("should apply the advanced match strategy when the user continues", () => {
+      testDialogAction("onContinue", UriMatchStrategy.StartsWith);
+    });
+
+    it("should revert to the previous strategy when the user cancels", () => {
+      testDialogAction("onCancel", UriMatchStrategy.Domain);
+    });
+  });
 });
diff --git a/libs/vault/src/cipher-form/components/autofill-options/uri-option.component.ts b/libs/vault/src/cipher-form/components/autofill-options/uri-option.component.ts
index 3f12382b931..4287d5b96c8 100644
--- a/libs/vault/src/cipher-form/components/autofill-options/uri-option.component.ts
+++ b/libs/vault/src/cipher-form/components/autofill-options/uri-option.component.ts
@@ -18,6 +18,7 @@ import {
   NG_VALUE_ACCESSOR,
   ReactiveFormsModule,
 } from "@angular/forms";
+import { concatMap, pairwise } from "rxjs";
 
 import { JslibModule } from "@bitwarden/angular/jslib.module";
 import {
@@ -26,12 +27,15 @@ import {
 } from "@bitwarden/common/models/domain/domain-service";
 import { I18nService } from "@bitwarden/common/platform/abstractions/i18n.service";
 import {
+  DialogService,
   FormFieldModule,
   IconButtonModule,
   SelectComponent,
   SelectModule,
 } from "@bitwarden/components";
 
+import { AdvancedUriOptionDialogComponent } from "./advanced-uri-option-dialog.component";
+
 @Component({
   selector: "vault-autofill-uri-option",
   templateUrl: "./uri-option.component.html",
@@ -65,16 +69,26 @@ export class UriOptionComponent implements ControlValueAccessor {
     matchDetection: [null as UriMatchStrategySetting],
   });
 
-  protected uriMatchOptions: { label: string; value: UriMatchStrategySetting }[] = [
+  protected uriMatchOptions: {
+    label: string;
+    value: UriMatchStrategySetting;
+    disabled?: boolean;
+  }[] = [
     { label: this.i18nService.t("default"), value: null },
     { label: this.i18nService.t("baseDomain"), value: UriMatchStrategy.Domain },
     { label: this.i18nService.t("host"), value: UriMatchStrategy.Host },
-    { label: this.i18nService.t("startsWith"), value: UriMatchStrategy.StartsWith },
-    { label: this.i18nService.t("regEx"), value: UriMatchStrategy.RegularExpression },
     { label: this.i18nService.t("exact"), value: UriMatchStrategy.Exact },
     { label: this.i18nService.t("never"), value: UriMatchStrategy.Never },
+    { label: this.i18nService.t("uriAdvancedOption"), value: null, disabled: true },
+    { label: this.i18nService.t("startsWith"), value: UriMatchStrategy.StartsWith },
+    { label: this.i18nService.t("regEx"), value: UriMatchStrategy.RegularExpression },
   ];
 
+  protected advancedOptionWarningMap: Partial<Record<UriMatchStrategySetting, string>> = {
+    [UriMatchStrategy.StartsWith]: "startsWithAdvancedOptionWarning",
+    [UriMatchStrategy.RegularExpression]: "regExAdvancedOptionWarning",
+  };
+
   /**
    * Whether the option can be reordered. If false, the reorder button will be hidden.
    */
@@ -147,6 +161,7 @@ export class UriOptionComponent implements ControlValueAccessor {
   }
 
   constructor(
+    private dialogService: DialogService,
     private formBuilder: FormBuilder,
     private i18nService: I18nService,
   ) {
@@ -157,6 +172,36 @@ export class UriOptionComponent implements ControlValueAccessor {
     this.uriForm.statusChanges.pipe(takeUntilDestroyed()).subscribe(() => {
       this.onTouched();
     });
+
+    this.uriForm.controls.matchDetection.valueChanges
+      .pipe(
+        pairwise(),
+        concatMap(([previous, current]) => this.handleAdvancedMatch(previous, current)),
+        takeUntilDestroyed(),
+      )
+      .subscribe();
+  }
+
+  private async handleAdvancedMatch(
+    previous: UriMatchStrategySetting,
+    current: UriMatchStrategySetting,
+  ) {
+    const valueChange = previous !== current;
+    const isAdvanced =
+      current === UriMatchStrategy.StartsWith || current === UriMatchStrategy.RegularExpression;
+
+    if (!valueChange || !isAdvanced) {
+      return;
+    }
+    AdvancedUriOptionDialogComponent.open(this.dialogService, {
+      contentKey: this.advancedOptionWarningMap[current],
+      onContinue: () => {
+        this.uriForm.controls.matchDetection.setValue(current);
+      },
+      onCancel: () => {
+        this.uriForm.controls.matchDetection.setValue(previous);
+      },
+    });
   }
 
   focusInput() {
@@ -193,4 +238,16 @@ export class UriOptionComponent implements ControlValueAccessor {
   setDisabledState?(isDisabled: boolean): void {
     isDisabled ? this.uriForm.disable() : this.uriForm.enable();
   }
+
+  getMatchHints() {
+    const hints = ["uriMatchDefaultStrategyHint"];
+    const strategy = this.uriForm.get("matchDetection")?.value;
+    if (
+      strategy === UriMatchStrategy.StartsWith ||
+      strategy === UriMatchStrategy.RegularExpression
+    ) {
+      hints.push(this.advancedOptionWarningMap[strategy]);
+    }
+    return hints;
+  }
 }