diff --git a/coderd/idpsync/idpsync.go b/coderd/idpsync/idpsync.go
index 2772a1b1ec..c57eee123b 100644
--- a/coderd/idpsync/idpsync.go
+++ b/coderd/idpsync/idpsync.go
@@ -251,13 +251,16 @@ type HTTPError struct {
 func (e HTTPError) Write(rw http.ResponseWriter, r *http.Request) {
 	if e.RenderStaticPage {
 		site.RenderStaticErrorPage(rw, r, site.ErrorPageData{
-			Status:       e.Code,
-			HideStatus:   true,
-			Title:        e.Msg,
-			Description:  e.Detail,
-			RetryEnabled: false,
-			DashboardURL: "/login",
-
+			Status:      e.Code,
+			HideStatus:  true,
+			Title:       e.Msg,
+			Description: e.Detail,
+			Actions: []site.Action{
+				{
+					URL:  "/login",
+					Text: "Back to site",
+				},
+			},
 			RenderDescriptionMarkdown: e.RenderDetailMarkdown,
 		})
 		return
diff --git a/coderd/oauth2provider/authorize.go b/coderd/oauth2provider/authorize.go
index d738e781e8..e5f6314b39 100644
--- a/coderd/oauth2provider/authorize.go
+++ b/coderd/oauth2provider/authorize.go
@@ -75,7 +75,18 @@ func ShowAuthorizePage(accessURL *url.URL) http.HandlerFunc {
 
 		callbackURL, err := url.Parse(app.CallbackURL)
 		if err != nil {
-			site.RenderStaticErrorPage(rw, r, site.ErrorPageData{Status: http.StatusInternalServerError, HideStatus: false, Title: "Internal Server Error", Description: err.Error(), RetryEnabled: false, DashboardURL: accessURL.String(), Warnings: nil})
+			site.RenderStaticErrorPage(rw, r, site.ErrorPageData{
+				Status:      http.StatusInternalServerError,
+				HideStatus:  false,
+				Title:       "Internal Server Error",
+				Description: err.Error(),
+				Actions: []site.Action{
+					{
+						URL:  accessURL.String(),
+						Text: "Back to site",
+					},
+				},
+			})
 			return
 		}
 
@@ -85,7 +96,19 @@ func ShowAuthorizePage(accessURL *url.URL) http.HandlerFunc {
 			for i, err := range validationErrs {
 				errStr[i] = err.Detail
 			}
-			site.RenderStaticErrorPage(rw, r, site.ErrorPageData{Status: http.StatusBadRequest, HideStatus: false, Title: "Invalid Query Parameters", Description: "One or more query parameters are missing or invalid.", RetryEnabled: false, DashboardURL: accessURL.String(), Warnings: errStr})
+			site.RenderStaticErrorPage(rw, r, site.ErrorPageData{
+				Status:      http.StatusBadRequest,
+				HideStatus:  false,
+				Title:       "Invalid Query Parameters",
+				Description: "One or more query parameters are missing or invalid.",
+				Warnings:    errStr,
+				Actions: []site.Action{
+					{
+						URL:  accessURL.String(),
+						Text: "Back to site",
+					},
+				},
+			})
 			return
 		}
 
diff --git a/coderd/tailnet.go b/coderd/tailnet.go
index cdcf657fe7..c83b26e001 100644
--- a/coderd/tailnet.go
+++ b/coderd/tailnet.go
@@ -199,10 +199,9 @@ func (s *ServerTailnet) ReverseProxy(targetURL, dashboardURL *url.URL, agentID u
 	proxy := httputil.NewSingleHostReverseProxy(&tgt)
 	proxy.ErrorHandler = func(w http.ResponseWriter, r *http.Request, theErr error) {
 		var (
-			desc                 = "Failed to proxy request to application: " + theErr.Error()
-			additionalInfo       = ""
-			additionalButtonLink = ""
-			additionalButtonText = ""
+			desc           = "Failed to proxy request to application: " + theErr.Error()
+			additionalInfo = ""
+			actions        = []site.Action{}
 		)
 
 		var tlsError tls.RecordHeaderError
@@ -222,21 +221,28 @@ func (s *ServerTailnet) ReverseProxy(targetURL, dashboardURL *url.URL, agentID u
 				app = app.ChangePortProtocol(targetProtocol)
 
 				switchURL.Host = fmt.Sprintf("%s%s", app.String(), strings.TrimPrefix(wildcardHostname, "*"))
-				additionalButtonLink = switchURL.String()
-				additionalButtonText = fmt.Sprintf("Switch to %s", strings.ToUpper(targetProtocol))
+				actions = append(actions, site.Action{
+					URL:  switchURL.String(),
+					Text: fmt.Sprintf("Switch to %s", strings.ToUpper(targetProtocol)),
+				})
 				additionalInfo += fmt.Sprintf("This error seems to be due to an app protocol mismatch, try switching to %s.", strings.ToUpper(targetProtocol))
 			}
 		}
 
 		site.RenderStaticErrorPage(w, r, site.ErrorPageData{
-			Status:               http.StatusBadGateway,
-			Title:                "Bad Gateway",
-			Description:          desc,
-			RetryEnabled:         true,
-			DashboardURL:         dashboardURL.String(),
-			AdditionalInfo:       additionalInfo,
-			AdditionalButtonLink: additionalButtonLink,
-			AdditionalButtonText: additionalButtonText,
+			Status:      http.StatusBadGateway,
+			Title:       "Bad Gateway",
+			Description: desc,
+			Actions: append(actions, []site.Action{
+				{
+					Text: "Retry",
+				},
+				{
+					URL:  dashboardURL.String(),
+					Text: "Back to site",
+				},
+			}...),
+			AdditionalInfo: additionalInfo,
 		})
 	}
 	proxy.Director = s.director(agentID, proxy.Director)
diff --git a/coderd/workspaceapps/errors.go b/coderd/workspaceapps/errors.go
index 64d61de367..f5cbdf1ef6 100644
--- a/coderd/workspaceapps/errors.go
+++ b/coderd/workspaceapps/errors.go
@@ -4,6 +4,7 @@ import (
 	"fmt"
 	"net/http"
 	"net/url"
+	"path"
 
 	"cdr.dev/slog"
 	"github.com/coder/coder/v2/codersdk"
@@ -30,12 +31,16 @@ func WriteWorkspaceApp404(log slog.Logger, accessURL *url.URL, rw http.ResponseW
 	}
 
 	site.RenderStaticErrorPage(rw, r, site.ErrorPageData{
-		Status:       http.StatusNotFound,
-		Title:        "Application Not Found",
-		Description:  "The application or workspace you are trying to access does not exist or you do not have permission to access it.",
-		RetryEnabled: false,
-		DashboardURL: accessURL.String(),
-		Warnings:     warnings,
+		Status:      http.StatusNotFound,
+		Title:       "Application Not Found",
+		Description: "The application or workspace you are trying to access does not exist or you do not have permission to access it.",
+		Warnings:    warnings,
+		Actions: []site.Action{
+			{
+				URL:  accessURL.String(),
+				Text: "Back to site",
+			},
+		},
 	})
 }
 
@@ -60,11 +65,15 @@ func WriteWorkspaceApp500(log slog.Logger, accessURL *url.URL, rw http.ResponseW
 	)
 
 	site.RenderStaticErrorPage(rw, r, site.ErrorPageData{
-		Status:       http.StatusInternalServerError,
-		Title:        "Internal Server Error",
-		Description:  "An internal server error occurred.",
-		RetryEnabled: false,
-		DashboardURL: accessURL.String(),
+		Status:      http.StatusInternalServerError,
+		Title:       "Internal Server Error",
+		Description: "An internal server error occurred.",
+		Actions: []site.Action{
+			{
+				URL:  accessURL.String(),
+				Text: "Back to site",
+			},
+		},
 	})
 }
 
@@ -85,11 +94,18 @@ func WriteWorkspaceAppOffline(log slog.Logger, accessURL *url.URL, rw http.Respo
 	}
 
 	site.RenderStaticErrorPage(rw, r, site.ErrorPageData{
-		Status:       http.StatusBadGateway,
-		Title:        "Application Unavailable",
-		Description:  msg,
-		RetryEnabled: true,
-		DashboardURL: accessURL.String(),
+		Status:      http.StatusBadGateway,
+		Title:       "Application Unavailable",
+		Description: msg,
+		Actions: []site.Action{
+			{
+				Text: "Retry",
+			},
+			{
+				URL:  accessURL.String(),
+				Text: "Back to site",
+			},
+		},
 	})
 }
 
@@ -109,11 +125,26 @@ func WriteWorkspaceOffline(log slog.Logger, accessURL *url.URL, rw http.Response
 		)
 	}
 
+	actions := []site.Action{
+		{
+			URL:  accessURL.String(),
+			Text: "Back to site",
+		},
+	}
+
+	workspaceURL, err := url.Parse(accessURL.String())
+	if err == nil {
+		workspaceURL.Path = path.Join(accessURL.Path, "@"+appReq.UsernameOrID, appReq.WorkspaceNameOrID)
+		actions = append(actions, site.Action{
+			URL:  workspaceURL.String(),
+			Text: "View workspace",
+		})
+	}
+
 	site.RenderStaticErrorPage(rw, r, site.ErrorPageData{
-		Status:       http.StatusBadRequest,
-		Title:        "Workspace Offline",
-		Description:  fmt.Sprintf("Last workspace transition was to the %q state. Start the workspace to access its applications.", codersdk.WorkspaceTransitionStop),
-		RetryEnabled: false,
-		DashboardURL: accessURL.String(),
+		Status:      http.StatusBadRequest,
+		Title:       "Workspace Offline",
+		Description: fmt.Sprintf("Last workspace transition was to the %q state. Start the workspace to access its applications.", codersdk.WorkspaceTransitionStop),
+		Actions:     actions,
 	})
 }
diff --git a/coderd/workspaceapps/proxy.go b/coderd/workspaceapps/proxy.go
index 981bba4584..8806841fb7 100644
--- a/coderd/workspaceapps/proxy.go
+++ b/coderd/workspaceapps/proxy.go
@@ -185,10 +185,14 @@ func (s *Server) handleAPIKeySmuggling(rw http.ResponseWriter, r *http.Request,
 			Status:      http.StatusBadRequest,
 			Title:       "Bad Request",
 			Description: "Could not decrypt API key. Workspace app API key smuggling is not permitted on the primary access URL. Please remove the query parameter and try again.",
-			// Retry is disabled because the user needs to remove the query
+			// No retry is included because the user needs to remove the query
 			// parameter before they try again.
-			RetryEnabled: false,
-			DashboardURL: s.DashboardURL.String(),
+			Actions: []site.Action{
+				{
+					URL:  s.DashboardURL.String(),
+					Text: "Back to site",
+				},
+			},
 		})
 		return false
 	}
@@ -204,10 +208,14 @@ func (s *Server) handleAPIKeySmuggling(rw http.ResponseWriter, r *http.Request,
 			Status:      http.StatusBadRequest,
 			Title:       "Bad Request",
 			Description: "Could not decrypt API key. Please remove the query parameter and try again.",
-			// Retry is disabled because the user needs to remove the query
+			// No retry is included because the user needs to remove the query
 			// parameter before they try again.
-			RetryEnabled: false,
-			DashboardURL: s.DashboardURL.String(),
+			Actions: []site.Action{
+				{
+					URL:  s.DashboardURL.String(),
+					Text: "Back to site",
+				},
+			},
 		})
 		return false
 	}
@@ -224,11 +232,15 @@ func (s *Server) handleAPIKeySmuggling(rw http.ResponseWriter, r *http.Request,
 			// startup, but we'll check anyways.
 			s.Logger.Error(r.Context(), "could not split invalid app hostname", slog.F("hostname", s.Hostname))
 			site.RenderStaticErrorPage(rw, r, site.ErrorPageData{
-				Status:       http.StatusInternalServerError,
-				Title:        "Internal Server Error",
-				Description:  "The app is configured with an invalid app wildcard hostname. Please contact an administrator.",
-				RetryEnabled: false,
-				DashboardURL: s.DashboardURL.String(),
+				Status:      http.StatusInternalServerError,
+				Title:       "Internal Server Error",
+				Description: "The app is configured with an invalid app wildcard hostname. Please contact an administrator.",
+				Actions: []site.Action{
+					{
+						URL:  s.DashboardURL.String(),
+						Text: "Back to site",
+					},
+				},
 			})
 			return false
 		}
@@ -274,11 +286,15 @@ func (s *Server) handleAPIKeySmuggling(rw http.ResponseWriter, r *http.Request,
 func (s *Server) workspaceAppsProxyPath(rw http.ResponseWriter, r *http.Request) {
 	if s.DisablePathApps {
 		site.RenderStaticErrorPage(rw, r, site.ErrorPageData{
-			Status:       http.StatusForbidden,
-			Title:        "Forbidden",
-			Description:  "Path-based applications are disabled on this Coder deployment by the administrator.",
-			RetryEnabled: false,
-			DashboardURL: s.DashboardURL.String(),
+			Status:      http.StatusForbidden,
+			Title:       "Forbidden",
+			Description: "Path-based applications are disabled on this Coder deployment by the administrator.",
+			Actions: []site.Action{
+				{
+					URL:  s.DashboardURL.String(),
+					Text: "Back to site",
+				},
+			},
 		})
 		return
 	}
@@ -287,11 +303,15 @@ func (s *Server) workspaceAppsProxyPath(rw http.ResponseWriter, r *http.Request)
 	// lookup the username from token. We used to redirect by doing this lookup.
 	if chi.URLParam(r, "user") == codersdk.Me {
 		site.RenderStaticErrorPage(rw, r, site.ErrorPageData{
-			Status:       http.StatusNotFound,
-			Title:        "Application Not Found",
-			Description:  "Applications must be accessed with the full username, not @me.",
-			RetryEnabled: false,
-			DashboardURL: s.DashboardURL.String(),
+			Status:      http.StatusNotFound,
+			Title:       "Application Not Found",
+			Description: "Applications must be accessed with the full username, not @me.",
+			Actions: []site.Action{
+				{
+					URL:  s.DashboardURL.String(),
+					Text: "Back to site",
+				},
+			},
 		})
 		return
 	}
@@ -519,11 +539,15 @@ func (s *Server) parseHostname(rw http.ResponseWriter, r *http.Request, next htt
 	app, err := appurl.ParseSubdomainAppURL(subdomain)
 	if err != nil {
 		site.RenderStaticErrorPage(rw, r, site.ErrorPageData{
-			Status:       http.StatusBadRequest,
-			Title:        "Invalid Application URL",
-			Description:  fmt.Sprintf("Could not parse subdomain application URL %q: %s", subdomain, err.Error()),
-			RetryEnabled: false,
-			DashboardURL: s.DashboardURL.String(),
+			Status:      http.StatusBadRequest,
+			Title:       "Invalid Application URL",
+			Description: fmt.Sprintf("Could not parse subdomain application URL %q: %s", subdomain, err.Error()),
+			Actions: []site.Action{
+				{
+					URL:  s.DashboardURL.String(),
+					Text: "Back to site",
+				},
+			},
 		})
 		return appurl.ApplicationURL{}, false
 	}
@@ -547,11 +571,18 @@ func (s *Server) proxyWorkspaceApp(rw http.ResponseWriter, r *http.Request, appT
 	appURL, err := url.Parse(appToken.AppURL)
 	if err != nil {
 		site.RenderStaticErrorPage(rw, r, site.ErrorPageData{
-			Status:       http.StatusBadRequest,
-			Title:        "Bad Request",
-			Description:  fmt.Sprintf("Application has an invalid URL %q: %s", appToken.AppURL, err.Error()),
-			RetryEnabled: true,
-			DashboardURL: s.DashboardURL.String(),
+			Status:      http.StatusBadRequest,
+			Title:       "Bad Request",
+			Description: fmt.Sprintf("Application has an invalid URL %q: %s", appToken.AppURL, err.Error()),
+			Actions: []site.Action{
+				{
+					Text: "Retry",
+				},
+				{
+					URL:  s.DashboardURL.String(),
+					Text: "Back to site",
+				},
+			},
 		})
 		return
 	}
diff --git a/enterprise/wsproxy/wsproxy.go b/enterprise/wsproxy/wsproxy.go
index ecd5df9cde..cfaa472242 100644
--- a/enterprise/wsproxy/wsproxy.go
+++ b/enterprise/wsproxy/wsproxy.go
@@ -379,8 +379,12 @@ func New(ctx context.Context, opts *Options) (*Server, error) {
 					HideStatus: true,
 					Description: "This workspace proxy is DERP-only and cannot be used for browser connections. " +
 						"Please use a different region directly from the dashboard. Click to be redirected!",
-					RetryEnabled: false,
-					DashboardURL: opts.DashboardURL.String(),
+					Actions: []site.Action{
+						{
+							URL:  opts.DashboardURL.String(),
+							Text: "Back to site",
+						},
+					},
 				})
 			}
 			serveDerpOnlyHandler := func(r chi.Router) {
@@ -422,8 +426,12 @@ func New(ctx context.Context, opts *Options) (*Server, error) {
 			HideStatus: true,
 			Description: "Workspace Proxies route traffic in terminals and apps directly to your workspace. " +
 				"This page must be loaded from the dashboard. Click to be redirected!",
-			RetryEnabled: false,
-			DashboardURL: opts.DashboardURL.String(),
+			Actions: []site.Action{
+				{
+					URL:  opts.DashboardURL.String(),
+					Text: "Back to site",
+				},
+			},
 		})
 	})
 
diff --git a/site/site.go b/site/site.go
index b91bde14cc..50b261ea72 100644
--- a/site/site.go
+++ b/site/site.go
@@ -933,20 +933,26 @@ func extractBin(dest string, r io.Reader) (numExtracted int, err error) {
 	}
 }
 
+// Action represents a link.
+type Action struct {
+	// URL is set as the href property on the anchor.  If empty, refreshes the
+	// page instead.
+	URL string
+	// Text is the displayed text of the button or link.
+	Text string
+}
+
 // ErrorPageData contains the variables that are found in
 // site/static/error.html.
 type ErrorPageData struct {
 	Status int
 	// HideStatus will remove the status code from the page.
-	HideStatus           bool
-	Title                string
-	Description          string
-	RetryEnabled         bool
-	DashboardURL         string
-	Warnings             []string
-	AdditionalInfo       string
-	AdditionalButtonLink string
-	AdditionalButtonText string
+	HideStatus     bool
+	Title          string
+	Description    string
+	Actions        []Action
+	Warnings       []string
+	AdditionalInfo string
 
 	RenderDescriptionMarkdown bool
 }
diff --git a/site/site_test.go b/site/site_test.go
index 36ec124ef8..4491c75af8 100644
--- a/site/site_test.go
+++ b/site/site_test.go
@@ -676,11 +676,18 @@ func TestRenderStaticErrorPage(t *testing.T) {
 	t.Parallel()
 
 	d := site.ErrorPageData{
-		Status:       http.StatusBadGateway,
-		Title:        "Bad Gateway 1234",
-		Description:  "shout out colin",
-		RetryEnabled: true,
-		DashboardURL: "https://example.com",
+		Status:      http.StatusBadGateway,
+		Title:       "Bad Gateway 1234",
+		Description: "shout out colin",
+		Actions: []site.Action{
+			{
+				Text: "Retry",
+			},
+			{
+				URL:  "https://example.com",
+				Text: "Back to site",
+			},
+		},
 	}
 
 	rw := httptest.NewRecorder()
@@ -699,19 +706,26 @@ func TestRenderStaticErrorPage(t *testing.T) {
 	require.Contains(t, bodyStr, d.Title)
 	require.Contains(t, bodyStr, d.Description)
 	require.Contains(t, bodyStr, "Retry")
-	require.Contains(t, bodyStr, d.DashboardURL)
+	require.Contains(t, bodyStr, "https://example.com")
 }
 
 func TestRenderStaticErrorPageNoStatus(t *testing.T) {
 	t.Parallel()
 
 	d := site.ErrorPageData{
-		HideStatus:   true,
-		Status:       http.StatusBadGateway,
-		Title:        "Bad Gateway 1234",
-		Description:  "shout out colin",
-		RetryEnabled: true,
-		DashboardURL: "https://example.com",
+		HideStatus:  true,
+		Status:      http.StatusBadGateway,
+		Title:       "Bad Gateway 1234",
+		Description: "shout out colin",
+		Actions: []site.Action{
+			{
+				Text: "Retry",
+			},
+			{
+				URL:  "https://example.com",
+				Text: "Back to site",
+			},
+		},
 	}
 
 	rw := httptest.NewRecorder()
@@ -730,7 +744,7 @@ func TestRenderStaticErrorPageNoStatus(t *testing.T) {
 	require.Contains(t, bodyStr, d.Title)
 	require.Contains(t, bodyStr, d.Description)
 	require.Contains(t, bodyStr, "Retry")
-	require.Contains(t, bodyStr, d.DashboardURL)
+	require.Contains(t, bodyStr, "https://example.com")
 }
 
 func TestJustFilesSystem(t *testing.T) {
diff --git a/site/static/error.html b/site/static/error.html
index bd73ed808f..22ea4d6f58 100644
--- a/site/static/error.html
+++ b/site/static/error.html
@@ -187,14 +187,18 @@
 				</ul>
 			</div>
 			{{ end }}
+
+			{{- if .Error.Actions }}
 			<div class="button-group">
-				{{- if and .Error.AdditionalButtonText .Error.AdditionalButtonLink }}
-				<a href="{{ .Error.AdditionalButtonLink }}">{{ .Error.AdditionalButtonText }}</a>
-				{{ end }} {{- if .Error.RetryEnabled }}
-				<button onclick="window.location.reload()">Retry</button>
-				{{ end }}
-				<a href="{{ .Error.DashboardURL }}">Back to site</a>
+				{{ range $i, $v := .Error.Actions }}
+				{{- if $v.URL }}
+				<a href="{{ $v.URL }}">{{ $v.Text }}</a>
+				{{ else }}
+				<button onclick="window.location.reload()">{{ $v.Text }}</button>
+				{{end}}
+				{{end}}
 			</div>
+			{{end}}
 		</div>
 	</body>
 </html>