diff --git a/apps/desktop/src/app/accounts/settings.component.html b/apps/desktop/src/app/accounts/settings.component.html
index bcbd9969f96..e56615c9122 100644
--- a/apps/desktop/src/app/accounts/settings.component.html
+++ b/apps/desktop/src/app/accounts/settings.component.html
@@ -440,6 +440,22 @@
                   "enableSshAgentDesc" | i18n
                 }}</small>
               </div>
+              <div class="form-group" *ngIf="this.form.value.enableSshAgent">
+                <label for="sshAgentPromptBehavior">{{ "sshAgentPromptBehavior" | i18n }}</label>
+                <select
+                  id="sshAgentPromptBehavior"
+                  aria-describedby="sshAgentPromptBehaviorHelp"
+                  formControlName="sshAgentPromptBehavior"
+                  (change)="saveSshAgentPromptBehavior()"
+                >
+                  <option *ngFor="let o of sshAgentPromptBehaviorOptions" [ngValue]="o.value">
+                    {{ o.name }}
+                  </option>
+                </select>
+                <small id="sshAgentPromptBehaviorHelp" class="help-block">{{
+                  "sshAgentPromptBehaviorDesc" | i18n
+                }}</small>
+              </div>
               <div class="form-group" *ngIf="!isLinux">
                 <div class="checkbox">
                   <label for="allowScreenshots">
diff --git a/apps/desktop/src/app/accounts/settings.component.spec.ts b/apps/desktop/src/app/accounts/settings.component.spec.ts
index b05d90b7e1c..6348ec30a97 100644
--- a/apps/desktop/src/app/accounts/settings.component.spec.ts
+++ b/apps/desktop/src/app/accounts/settings.component.spec.ts
@@ -33,6 +33,7 @@ import { UserId } from "@bitwarden/common/types/guid";
 import { DialogService } from "@bitwarden/components";
 import { BiometricStateService, BiometricsStatus, KeyService } from "@bitwarden/key-management";
 
+import { SshAgentPromptType } from "../../autofill/models/ssh-agent-setting";
 import { DesktopAutofillSettingsService } from "../../autofill/services/desktop-autofill-settings.service";
 import { DesktopBiometricsService } from "../../key-management/biometrics/desktop.biometrics.service";
 import { DesktopSettingsService } from "../../platform/services/desktop-settings.service";
@@ -139,6 +140,7 @@ describe("SettingsComponent", () => {
     desktopSettingsService.browserIntegrationFingerprintEnabled$ = of(false);
     desktopSettingsService.hardwareAcceleration$ = of(false);
     desktopSettingsService.sshAgentEnabled$ = of(false);
+    desktopSettingsService.sshAgentPromptBehavior$ = of(SshAgentPromptType.Always);
     desktopSettingsService.preventScreenshots$ = of(false);
     domainSettingsService.showFavicons$ = of(false);
     desktopAutofillSettingsService.enableDuckDuckGoBrowserIntegration$ = of(false);
diff --git a/apps/desktop/src/app/accounts/settings.component.ts b/apps/desktop/src/app/accounts/settings.component.ts
index a592e542d58..2639d819854 100644
--- a/apps/desktop/src/app/accounts/settings.component.ts
+++ b/apps/desktop/src/app/accounts/settings.component.ts
@@ -45,6 +45,7 @@ import { DialogService } from "@bitwarden/components";
 import { KeyService, BiometricStateService, BiometricsStatus } from "@bitwarden/key-management";
 
 import { SetPinComponent } from "../../auth/components/set-pin.component";
+import { SshAgentPromptType } from "../../autofill/models/ssh-agent-setting";
 import { DesktopAutofillSettingsService } from "../../autofill/services/desktop-autofill-settings.service";
 import { DesktopBiometricsService } from "../../key-management/biometrics/desktop.biometrics.service";
 import { DesktopSettingsService } from "../../platform/services/desktop-settings.service";
@@ -63,6 +64,7 @@ export class SettingsComponent implements OnInit, OnDestroy {
   localeOptions: any[];
   themeOptions: any[];
   clearClipboardOptions: any[];
+  sshAgentPromptBehaviorOptions: any[];
   supportsBiometric: boolean;
   private timerId: any;
   showAlwaysShowDock = false;
@@ -126,6 +128,7 @@ export class SettingsComponent implements OnInit, OnDestroy {
     }),
     enableHardwareAcceleration: true,
     enableSshAgent: false,
+    sshAgentPromptBehavior: SshAgentPromptType.Always,
     allowScreenshots: false,
     enableDuckDuckGoBrowserIntegration: false,
     theme: [null as Theme | null],
@@ -212,6 +215,17 @@ export class SettingsComponent implements OnInit, OnDestroy {
       { name: this.i18nService.t("twoMinutes"), value: 120 },
       { name: this.i18nService.t("fiveMinutes"), value: 300 },
     ];
+    this.sshAgentPromptBehaviorOptions = [
+      {
+        name: this.i18nService.t("sshAgentPromptBehaviorAlways"),
+        value: SshAgentPromptType.Always,
+      },
+      { name: this.i18nService.t("sshAgentPromptBehaviorNever"), value: SshAgentPromptType.Never },
+      {
+        name: this.i18nService.t("sshAgentPromptBehaviorRememberUntilLock"),
+        value: SshAgentPromptType.RememberUntilLock,
+      },
+    ];
   }
 
   async ngOnInit() {
@@ -312,6 +326,9 @@ export class SettingsComponent implements OnInit, OnDestroy {
         this.desktopSettingsService.hardwareAcceleration$,
       ),
       enableSshAgent: await firstValueFrom(this.desktopSettingsService.sshAgentEnabled$),
+      sshAgentPromptBehavior: await firstValueFrom(
+        this.desktopSettingsService.sshAgentPromptBehavior$,
+      ),
       allowScreenshots: !(await firstValueFrom(this.desktopSettingsService.preventScreenshots$)),
       theme: await firstValueFrom(this.themeStateService.selectedTheme$),
       locale: await firstValueFrom(this.i18nService.userSetLocale$),
@@ -779,10 +796,15 @@ export class SettingsComponent implements OnInit, OnDestroy {
   }
 
   async saveSshAgent() {
-    this.logService.debug("Saving Ssh Agent settings", this.form.value.enableSshAgent);
     await this.desktopSettingsService.setSshAgentEnabled(this.form.value.enableSshAgent);
   }
 
+  async saveSshAgentPromptBehavior() {
+    await this.desktopSettingsService.setSshAgentPromptBehavior(
+      this.form.value.sshAgentPromptBehavior,
+    );
+  }
+
   async savePreventScreenshots() {
     await this.desktopSettingsService.setPreventScreenshots(!this.form.value.allowScreenshots);
 
diff --git a/apps/desktop/src/autofill/models/ssh-agent-setting.ts b/apps/desktop/src/autofill/models/ssh-agent-setting.ts
new file mode 100644
index 00000000000..f332cc93ee1
--- /dev/null
+++ b/apps/desktop/src/autofill/models/ssh-agent-setting.ts
@@ -0,0 +1,5 @@
+export enum SshAgentPromptType {
+  Always = "always",
+  Never = "never",
+  RememberUntilLock = "rememberUntilLock",
+}
diff --git a/apps/desktop/src/autofill/services/ssh-agent.service.ts b/apps/desktop/src/autofill/services/ssh-agent.service.ts
index 6522ef19500..d6ae5b0ffa2 100644
--- a/apps/desktop/src/autofill/services/ssh-agent.service.ts
+++ b/apps/desktop/src/autofill/services/ssh-agent.service.ts
@@ -34,6 +34,7 @@ import { DialogService, ToastService } from "@bitwarden/components";
 
 import { ApproveSshRequestComponent } from "../../platform/components/approve-ssh-request";
 import { DesktopSettingsService } from "../../platform/services/desktop-settings.service";
+import { SshAgentPromptType } from "../models/ssh-agent-setting";
 
 @Injectable({
   providedIn: "root",
@@ -43,6 +44,8 @@ export class SshAgentService implements OnDestroy {
   SSH_VAULT_UNLOCK_REQUEST_TIMEOUT = 60_000;
   SSH_REQUEST_UNLOCK_POLLING_INTERVAL = 100;
 
+  private authorizedSshKeys: Record<string, Date> = {};
+
   private isFeatureFlagEnabled = false;
 
   private destroy$ = new Subject<void>();
@@ -166,19 +169,26 @@ export class SshAgentService implements OnDestroy {
               .catch((e) => this.logService.error("Failed to respond to SSH request", e));
           }
 
-          const cipher = ciphers.find((cipher) => cipher.id == cipherId);
+          if (await this.needsAuthorization(cipherId, isAgentForwarding)) {
+            ipc.platform.focusWindow();
+            const cipher = ciphers.find((cipher) => cipher.id == cipherId);
+            const dialogRef = ApproveSshRequestComponent.open(
+              this.dialogService,
+              cipher.name,
+              application,
+              isAgentForwarding,
+              namespace,
+            );
 
-          ipc.platform.focusWindow();
-          const dialogRef = ApproveSshRequestComponent.open(
-            this.dialogService,
-            cipher.name,
-            application,
-            isAgentForwarding,
-            namespace,
-          );
-
-          const result = await firstValueFrom(dialogRef.closed);
-          return ipc.platform.sshAgent.signRequestResponse(requestId, result);
+            if (await firstValueFrom(dialogRef.closed)) {
+              await this.rememberAuthorization(cipherId);
+              return ipc.platform.sshAgent.signRequestResponse(requestId, true);
+            } else {
+              return ipc.platform.sshAgent.signRequestResponse(requestId, false);
+            }
+          } else {
+            return ipc.platform.sshAgent.signRequestResponse(requestId, true);
+          }
         }),
         takeUntil(this.destroy$),
       )
@@ -190,6 +200,7 @@ export class SshAgentService implements OnDestroy {
           return;
         }
 
+        this.authorizedSshKeys = {};
         this.logService.info("Active account changed, clearing SSH keys");
         ipc.platform.sshAgent
           .clearKeys()
@@ -211,6 +222,7 @@ export class SshAgentService implements OnDestroy {
         }
 
         this.logService.info("Active account observable completed, clearing SSH keys");
+        this.authorizedSshKeys = {};
         ipc.platform.sshAgent
           .clearKeys()
           .catch((e) => this.logService.error("Failed to clear SSH keys", e));
@@ -270,4 +282,25 @@ export class SshAgentService implements OnDestroy {
     this.destroy$.next();
     this.destroy$.complete();
   }
+
+  private async rememberAuthorization(cipherId: string): Promise<void> {
+    this.authorizedSshKeys[cipherId] = new Date();
+  }
+
+  private async needsAuthorization(cipherId: string, isForward: boolean): Promise<boolean> {
+    // Agent forwarding ALWAYS needs authorization because it is a remote machine
+    if (isForward) {
+      return true;
+    }
+
+    const promptType = await firstValueFrom(this.desktopSettingsService.sshAgentPromptBehavior$);
+    switch (promptType) {
+      case SshAgentPromptType.Never:
+        return false;
+      case SshAgentPromptType.Always:
+        return true;
+      case SshAgentPromptType.RememberUntilLock:
+        return !(cipherId in this.authorizedSshKeys);
+    }
+  }
 }
diff --git a/apps/desktop/src/locales/en/messages.json b/apps/desktop/src/locales/en/messages.json
index e705b5e787a..50620c106f5 100644
--- a/apps/desktop/src/locales/en/messages.json
+++ b/apps/desktop/src/locales/en/messages.json
@@ -237,6 +237,24 @@
   "enableSshAgentHelp": {
     "message": "The SSH agent is a service targeted at developers that allows you to sign SSH requests directly from your Bitwarden vault."
   },
+  "sshAgentPromptBehavior": {
+    "message": "Ask for authorization when using SSH agent"
+  },
+  "sshAgentPromptBehaviorDesc": {
+    "message": "Choose how to handle SSH-agent authorization requests."
+  },
+  "sshAgentPromptBehaviorHelp": {
+    "message": "Remember SSH authorizations"
+  },
+  "sshAgentPromptBehaviorAlways": {
+    "message": "Always"
+  },
+  "sshAgentPromptBehaviorNever": {
+    "message": "Never"
+  },
+  "sshAgentPromptBehaviorRememberUntilLock": {
+    "message": "Remember until vault is locked"
+  },
   "premiumRequired": {
     "message": "Premium required"
   },
diff --git a/apps/desktop/src/platform/services/desktop-settings.service.ts b/apps/desktop/src/platform/services/desktop-settings.service.ts
index f5789d6f40c..37a1fe73829 100644
--- a/apps/desktop/src/platform/services/desktop-settings.service.ts
+++ b/apps/desktop/src/platform/services/desktop-settings.service.ts
@@ -8,6 +8,7 @@ import {
 } from "@bitwarden/common/platform/state";
 import { UserId } from "@bitwarden/common/types/guid";
 
+import { SshAgentPromptType } from "../../autofill/models/ssh-agent-setting";
 import { ModalModeState, WindowState } from "../models/domain/window-state";
 
 export const HARDWARE_ACCELERATION = new KeyDefinition<boolean>(
@@ -70,6 +71,15 @@ const SSH_AGENT_ENABLED = new KeyDefinition<boolean>(DESKTOP_SETTINGS_DISK, "ssh
   deserializer: (b) => b,
 });
 
+const SSH_AGENT_PROMPT_BEHAVIOR = new UserKeyDefinition<SshAgentPromptType>(
+  DESKTOP_SETTINGS_DISK,
+  "sshAgentRememberAuthorizations",
+  {
+    deserializer: (b) => b,
+    clearOn: [],
+  },
+);
+
 const MINIMIZE_ON_COPY = new UserKeyDefinition<boolean>(DESKTOP_SETTINGS_DISK, "minimizeOnCopy", {
   deserializer: (b) => b,
   clearOn: [], // User setting, no need to clear
@@ -159,6 +169,11 @@ export class DesktopSettingsService {
 
   sshAgentEnabled$ = this.sshAgentEnabledState.state$.pipe(map(Boolean));
 
+  private readonly sshAgentPromptBehavior = this.stateProvider.getActive(SSH_AGENT_PROMPT_BEHAVIOR);
+  sshAgentPromptBehavior$ = this.sshAgentPromptBehavior.state$.pipe(
+    map((v) => v ?? SshAgentPromptType.Always),
+  );
+
   private readonly preventScreenshotState = this.stateProvider.getGlobal(PREVENT_SCREENSHOTS);
 
   /**
@@ -292,6 +307,10 @@ export class DesktopSettingsService {
     await this.sshAgentEnabledState.update(() => value);
   }
 
+  async setSshAgentPromptBehavior(value: SshAgentPromptType) {
+    await this.sshAgentPromptBehavior.update(() => value);
+  }
+
   /**
    * Sets the minimize on copy value for the current user.
    * @param value `true` if the application should minimize when a value is copied,