diff --git a/components/dashboard/src/projects/Prebuild.tsx b/components/dashboard/src/projects/Prebuild.tsx
index c36ffd7e58987d..e46ad41e96f455 100644
--- a/components/dashboard/src/projects/Prebuild.tsx
+++ b/components/dashboard/src/projects/Prebuild.tsx
@@ -156,39 +156,42 @@ export default function () {
             <Header title={renderTitle()} subtitle={renderSubtitle()} />
             <div className="app-container mt-8">
                 <PrebuildLogs workspaceId={prebuild?.info?.buildWorkspaceId}>
-                    {["aborted", "timeout", "failed"].includes(prebuild?.status || "") || !!prebuild?.error ? (
-                        <button
-                            className="flex items-center space-x-2"
-                            disabled={isRerunningPrebuild}
-                            onClick={rerunPrebuild}
-                        >
-                            {isRerunningPrebuild && (
-                                <img className="h-4 w-4 animate-spin filter brightness-150" src={Spinner} />
-                            )}
-                            <span>Rerun Prebuild ({prebuild?.info.branch})</span>
-                        </button>
-                    ) : ["building", "queued"].includes(prebuild?.status || "") ? (
+                    {["building", "queued"].includes(prebuild?.status || "") ? (
                         <button
                             className="danger flex items-center space-x-2"
                             disabled={isCancellingPrebuild}
                             onClick={cancelPrebuild}
                         >
                             {isCancellingPrebuild && (
-                                <img className="h-4 w-4 animate-spin filter brightness-150" src={Spinner} />
+                                <img alt="" className="h-4 w-4 animate-spin filter brightness-150" src={Spinner} />
                             )}
                             <span>Cancel Prebuild</span>
                         </button>
-                    ) : prebuild?.status === "available" ? (
-                        <a
-                            className="my-auto"
-                            href={gitpodHostUrl
-                                .withContext(`open-prebuild/${prebuild?.info.id}/${prebuild?.info.changeUrl}`)
-                                .toString()}
-                        >
-                            <button>New Workspace (with this prebuild)</button>
-                        </a>
                     ) : (
-                        <button disabled={true}>New Workspace (with this prebuild)</button>
+                        <>
+                            <button
+                                className="secondary flex items-center space-x-2"
+                                disabled={isRerunningPrebuild}
+                                onClick={rerunPrebuild}
+                            >
+                                {isRerunningPrebuild && (
+                                    <img alt="" className="h-4 w-4 animate-spin filter brightness-150" src={Spinner} />
+                                )}
+                                <span>Rerun Prebuild ({prebuild?.info.branch})</span>
+                            </button>
+                            {prebuild?.status === "available" ? (
+                                <a
+                                    className="my-auto"
+                                    href={gitpodHostUrl
+                                        .withContext(`open-prebuild/${prebuild?.info.id}/${prebuild?.info.changeUrl}`)
+                                        .toString()}
+                                >
+                                    <button>New Workspace (with this prebuild)</button>
+                                </a>
+                            ) : (
+                                <button disabled={true}>New Workspace (with this prebuild)</button>
+                            )}
+                        </>
                     )}
                 </PrebuildLogs>
             </div>
diff --git a/components/dashboard/src/projects/Prebuilds.tsx b/components/dashboard/src/projects/Prebuilds.tsx
index e86d47e1698dd5..570e5145b5fb4b 100644
--- a/components/dashboard/src/projects/Prebuilds.tsx
+++ b/components/dashboard/src/projects/Prebuilds.tsx
@@ -39,6 +39,7 @@ export default function (props: { project?: Project; isAdminDashboard?: boolean
 
     const [isLoadingPrebuilds, setIsLoadingPrebuilds] = useState<boolean>(true);
     const [prebuilds, setPrebuilds] = useState<PrebuildWithStatus[]>([]);
+    const [isRunningPrebuild, setIsRunningPrebuild] = useState<boolean>(false);
 
     useEffect(() => {
         let registration: Disposable;
@@ -139,11 +140,18 @@ export default function (props: { project?: Project; isAdminDashboard?: boolean
         return -1;
     };
 
-    const triggerPrebuild = (branchName: string | null) => {
+    const runPrebuild = async (branchName: string | null) => {
         if (!project) {
             return;
         }
-        getGitpodService().server.triggerPrebuild(project.id, branchName);
+        setIsRunningPrebuild(true);
+        try {
+            await getGitpodService().server.triggerPrebuild(project.id, branchName);
+        } catch (error) {
+            console.error("Could not run prebuild", error);
+        } finally {
+            setIsRunningPrebuild(false);
+        }
     };
 
     const formatDate = (date: string | undefined) => {
@@ -182,9 +190,16 @@ export default function (props: { project?: Project; isAdminDashboard?: boolean
                     <div className="py-3 pl-3">
                         <DropDown prefix="Prebuild Status: " customClasses="w-32" entries={statusFilterEntries()} />
                     </div>
-                    {!isLoadingPrebuilds && prebuilds.length === 0 && !props.isAdminDashboard && (
-                        <button onClick={() => triggerPrebuild(null)} className="ml-2">
-                            Run Prebuild
+                    {!props.isAdminDashboard && (
+                        <button
+                            onClick={() => runPrebuild(null)}
+                            disabled={isRunningPrebuild}
+                            className="ml-2 flex items-center space-x-2"
+                        >
+                            {isRunningPrebuild && (
+                                <img alt="" className="h-4 w-4 animate-spin filter brightness-150" src={Spinner} />
+                            )}
+                            <span>Run Prebuild</span>
                         </button>
                     )}
                 </div>
diff --git a/components/dashboard/src/projects/Project.tsx b/components/dashboard/src/projects/Project.tsx
index a39d64aa916c5b..99e3bf7324dae0 100644
--- a/components/dashboard/src/projects/Project.tsx
+++ b/components/dashboard/src/projects/Project.tsx
@@ -388,20 +388,7 @@ export default function () {
                                                 <ItemFieldContextMenu
                                                     className="py-0.5"
                                                     menuEntries={
-                                                        !prebuild ||
-                                                        prebuild.status === "aborted" ||
-                                                        prebuild.status === "failed" ||
-                                                        prebuild.status === "timeout" ||
-                                                        !!prebuild.error
-                                                            ? [
-                                                                  {
-                                                                      title: `${prebuild ? "Rerun" : "Run"} Prebuild (${
-                                                                          branch.name
-                                                                      })`,
-                                                                      onClick: () => triggerPrebuild(branch),
-                                                                  },
-                                                              ]
-                                                            : prebuild.status === "building"
+                                                        prebuild?.status === "queued" || prebuild?.status === "building"
                                                             ? [
                                                                   {
                                                                       title: "Cancel Prebuild",
@@ -411,7 +398,14 @@ export default function () {
                                                                           prebuild && cancelPrebuild(prebuild.info.id),
                                                                   },
                                                               ]
-                                                            : []
+                                                            : [
+                                                                  {
+                                                                      title: `${prebuild ? "Rerun" : "Run"} Prebuild (${
+                                                                          branch.name
+                                                                      })`,
+                                                                      onClick: () => triggerPrebuild(branch),
+                                                                  },
+                                                              ]
                                                     }
                                                 />
                                             </ItemField>
diff --git a/components/server/ee/src/prebuilds/prebuild-manager.ts b/components/server/ee/src/prebuilds/prebuild-manager.ts
index 167ed9f1d4a6bc..be6ba74e81ab12 100644
--- a/components/server/ee/src/prebuilds/prebuild-manager.ts
+++ b/components/server/ee/src/prebuilds/prebuild-manager.ts
@@ -134,34 +134,37 @@ export class PrebuildManager {
                     `Running prebuilds without a project is no longer supported. Please add '${cloneURL}' as a project in a Gitpod team.`,
                 );
             }
-            const existingPB = await this.findNonFailedPrebuiltWorkspace({ span }, cloneURL, commitSHAIdentifier);
 
-            // If the existing prebuild is failed, it will be retriggered in the afterwards
             const config = await this.fetchConfig({ span }, user, context);
-            if (existingPB) {
-                // If the existing prebuild is based on an outdated project config, we also want to retrigger it.
-                const existingPBWS = await this.workspaceDB.trace({ span }).findById(existingPB.buildWorkspaceId);
-                const existingConfig = existingPBWS?.config;
-                log.debug(
-                    `startPrebuild | commits: ${commitSHAIdentifier}, existingPB: ${
-                        existingPB.id
-                    }, existingConfig: ${JSON.stringify(existingConfig)}, newConfig: ${JSON.stringify(config)}}`,
-                );
-                const filterPrebuildTasks = (tasks: TaskConfig[] = []) =>
-                    tasks
-                        .map((task) =>
-                            Object.keys(task)
-                                .filter((key) => ["before", "init", "prebuild"].includes(key))
-                                // @ts-ignore
-                                .reduce((obj, key) => ({ ...obj, [key]: task[key] }), {}),
-                        )
-                        .filter((task) => Object.keys(task).length > 0);
-                const isSameConfig =
-                    JSON.stringify(filterPrebuildTasks(existingConfig?.tasks)) ===
-                    JSON.stringify(filterPrebuildTasks(config?.tasks));
-                // If there is an existing prebuild that isn't failed and it's based on the current config, we return it here instead of triggering a new prebuild.
-                if (isSameConfig) {
-                    return { prebuildId: existingPB.id, wsid: existingPB.buildWorkspaceId, done: true };
+
+            if (!forcePrebuild) {
+                // Check for an existing, successful prebuild, before triggering a new one.
+                const existingPB = await this.findNonFailedPrebuiltWorkspace({ span }, cloneURL, commitSHAIdentifier);
+                if (existingPB) {
+                    // But if the existing prebuild is failed, or based on an outdated config, it will still be retriggered below.
+                    const existingPBWS = await this.workspaceDB.trace({ span }).findById(existingPB.buildWorkspaceId);
+                    const existingConfig = existingPBWS?.config;
+                    log.debug(
+                        `startPrebuild | commits: ${commitSHAIdentifier}, existingPB: ${
+                            existingPB.id
+                        }, existingConfig: ${JSON.stringify(existingConfig)}, newConfig: ${JSON.stringify(config)}}`,
+                    );
+                    const filterPrebuildTasks = (tasks: TaskConfig[] = []) =>
+                        tasks
+                            .map((task) =>
+                                Object.keys(task)
+                                    .filter((key) => ["before", "init", "prebuild"].includes(key))
+                                    // @ts-ignore
+                                    .reduce((obj, key) => ({ ...obj, [key]: task[key] }), {}),
+                            )
+                            .filter((task) => Object.keys(task).length > 0);
+                    const isSameConfig =
+                        JSON.stringify(filterPrebuildTasks(existingConfig?.tasks)) ===
+                        JSON.stringify(filterPrebuildTasks(config?.tasks));
+                    // If there is an existing prebuild that isn't failed and it's based on the current config, we return it here instead of triggering a new prebuild.
+                    if (isSameConfig) {
+                        return { prebuildId: existingPB.id, wsid: existingPB.buildWorkspaceId, done: true };
+                    }
                 }
             }
             if (project && context.ref && !project.settings?.keepOutdatedPrebuildsRunning) {