diff --git a/cli/configssh.go b/cli/configssh.go
index cdaf404ab50df..a7aed33eba1df 100644
--- a/cli/configssh.go
+++ b/cli/configssh.go
@@ -3,7 +3,6 @@ package cli
 import (
 	"bufio"
 	"bytes"
-	"context"
 	"errors"
 	"fmt"
 	"io"
@@ -12,7 +11,6 @@ import (
 	"os"
 	"path/filepath"
 	"runtime"
-	"sort"
 	"strconv"
 	"strings"
 
@@ -22,11 +20,9 @@ import (
 	"github.com/pkg/diff/write"
 	"golang.org/x/exp/constraints"
 	"golang.org/x/exp/slices"
-	"golang.org/x/sync/errgroup"
 	"golang.org/x/xerrors"
 
 	"github.com/coder/coder/v2/cli/cliui"
-	"github.com/coder/coder/v2/coderd/util/slice"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/serpent"
 )
@@ -139,74 +135,6 @@ func (o sshConfigOptions) asList() (list []string) {
 	return list
 }
 
-type sshWorkspaceConfig struct {
-	Name  string
-	Hosts []string
-}
-
-func sshFetchWorkspaceConfigs(ctx context.Context, client *codersdk.Client) ([]sshWorkspaceConfig, error) {
-	res, err := client.Workspaces(ctx, codersdk.WorkspaceFilter{
-		Owner: codersdk.Me,
-	})
-	if err != nil {
-		return nil, err
-	}
-
-	var errGroup errgroup.Group
-	workspaceConfigs := make([]sshWorkspaceConfig, len(res.Workspaces))
-	for i, workspace := range res.Workspaces {
-		i := i
-		workspace := workspace
-		errGroup.Go(func() error {
-			resources, err := client.TemplateVersionResources(ctx, workspace.LatestBuild.TemplateVersionID)
-			if err != nil {
-				return err
-			}
-
-			wc := sshWorkspaceConfig{Name: workspace.Name}
-			var agents []codersdk.WorkspaceAgent
-			for _, resource := range resources {
-				if resource.Transition != codersdk.WorkspaceTransitionStart {
-					continue
-				}
-				agents = append(agents, resource.Agents...)
-			}
-
-			// handle both WORKSPACE and WORKSPACE.AGENT syntax
-			if len(agents) == 1 {
-				wc.Hosts = append(wc.Hosts, workspace.Name)
-			}
-			for _, agent := range agents {
-				hostname := workspace.Name + "." + agent.Name
-				wc.Hosts = append(wc.Hosts, hostname)
-			}
-
-			workspaceConfigs[i] = wc
-
-			return nil
-		})
-	}
-	err = errGroup.Wait()
-	if err != nil {
-		return nil, err
-	}
-
-	return workspaceConfigs, nil
-}
-
-func sshPrepareWorkspaceConfigs(ctx context.Context, client *codersdk.Client) (receive func() ([]sshWorkspaceConfig, error)) {
-	wcC := make(chan []sshWorkspaceConfig, 1)
-	errC := make(chan error, 1)
-	go func() {
-		wc, err := sshFetchWorkspaceConfigs(ctx, client)
-		wcC <- wc
-		errC <- err
-	}()
-	return func() ([]sshWorkspaceConfig, error) {
-		return <-wcC, <-errC
-	}
-}
-
 func (r *RootCmd) configSSH() *serpent.Command {
 	var (
 		sshConfigFile       string
@@ -254,8 +182,6 @@ func (r *RootCmd) configSSH() *serpent.Command {
 			// warning at any time.
 			_, _ = client.BuildInfo(ctx)
 
-			recvWorkspaceConfigs := sshPrepareWorkspaceConfigs(ctx, client)
-
 			out := inv.Stdout
 			if dryRun {
 				// Print everything except diff to stderr so
@@ -371,11 +297,6 @@ func (r *RootCmd) configSSH() *serpent.Command {
 			newline := len(before) > 0
 			sshConfigWriteSectionHeader(buf, newline, sshConfigOpts)
 
-			workspaceConfigs, err := recvWorkspaceConfigs()
-			if err != nil {
-				return xerrors.Errorf("fetch workspace configs failed: %w", err)
-			}
-
 			coderdConfig, err := client.SSHConfiguration(ctx)
 			if err != nil {
 				// If the error is 404, this deployment does not support
@@ -394,91 +315,79 @@ func (r *RootCmd) configSSH() *serpent.Command {
 				coderdConfig.HostnamePrefix = sshConfigOpts.userHostPrefix
 			}
 
-			// Ensure stable sorting of output.
-			slices.SortFunc(workspaceConfigs, func(a, b sshWorkspaceConfig) int {
-				return slice.Ascending(a.Name, b.Name)
-			})
-			for _, wc := range workspaceConfigs {
-				sort.Strings(wc.Hosts)
-				// Write agent configuration.
-				for _, workspaceHostname := range wc.Hosts {
-					sshHostname := fmt.Sprintf("%s%s", coderdConfig.HostnamePrefix, workspaceHostname)
-					defaultOptions := []string{
-						"HostName " + sshHostname,
-						"ConnectTimeout=0",
-						"StrictHostKeyChecking=no",
-						// Without this, the "REMOTE HOST IDENTITY CHANGED"
-						// message will appear.
-						"UserKnownHostsFile=/dev/null",
-						// This disables the "Warning: Permanently added 'hostname' (RSA) to the list of known hosts."
-						// message from appearing on every SSH. This happens because we ignore the known hosts.
-						"LogLevel ERROR",
-					}
-
-					if !skipProxyCommand {
-						rootFlags := fmt.Sprintf("--global-config %s", escapedGlobalConfig)
-						for _, h := range sshConfigOpts.header {
-							rootFlags += fmt.Sprintf(" --header %q", h)
-						}
-						if sshConfigOpts.headerCommand != "" {
-							rootFlags += fmt.Sprintf(" --header-command %q", sshConfigOpts.headerCommand)
-						}
-
-						flags := ""
-						if sshConfigOpts.waitEnum != "auto" {
-							flags += " --wait=" + sshConfigOpts.waitEnum
-						}
-						if sshConfigOpts.disableAutostart {
-							flags += " --disable-autostart=true"
-						}
-						defaultOptions = append(defaultOptions, fmt.Sprintf(
-							"ProxyCommand %s %s ssh --stdio%s %s",
-							escapedCoderBinary, rootFlags, flags, workspaceHostname,
-						))
-					}
+			// Write agent configuration.
+			defaultOptions := []string{
+				"ConnectTimeout=0",
+				"StrictHostKeyChecking=no",
+				// Without this, the "REMOTE HOST IDENTITY CHANGED"
+				// message will appear.
+				"UserKnownHostsFile=/dev/null",
+				// This disables the "Warning: Permanently added 'hostname' (RSA) to the list of known hosts."
+				// message from appearing on every SSH. This happens because we ignore the known hosts.
+				"LogLevel ERROR",
+			}
 
-					// Create a copy of the options so we can modify them.
-					configOptions := sshConfigOpts
-					configOptions.sshOptions = nil
-
-					// User options first (SSH only uses the first
-					// option unless it can be given multiple times)
-					for _, opt := range sshConfigOpts.sshOptions {
-						err := configOptions.addOptions(opt)
-						if err != nil {
-							return xerrors.Errorf("add flag config option %q: %w", opt, err)
-						}
-					}
+			if !skipProxyCommand {
+				rootFlags := fmt.Sprintf("--global-config %s", escapedGlobalConfig)
+				for _, h := range sshConfigOpts.header {
+					rootFlags += fmt.Sprintf(" --header %q", h)
+				}
+				if sshConfigOpts.headerCommand != "" {
+					rootFlags += fmt.Sprintf(" --header-command %q", sshConfigOpts.headerCommand)
+				}
 
-					// Deployment options second, allow them to
-					// override standard options.
-					for k, v := range coderdConfig.SSHConfigOptions {
-						opt := fmt.Sprintf("%s %s", k, v)
-						err := configOptions.addOptions(opt)
-						if err != nil {
-							return xerrors.Errorf("add coderd config option %q: %w", opt, err)
-						}
-					}
+				flags := ""
+				if sshConfigOpts.waitEnum != "auto" {
+					flags += " --wait=" + sshConfigOpts.waitEnum
+				}
+				if sshConfigOpts.disableAutostart {
+					flags += " --disable-autostart=true"
+				}
+				defaultOptions = append(defaultOptions, fmt.Sprintf(
+					"ProxyCommand %s %s ssh --stdio%s --ssh-host-prefix %s %%h",
+					escapedCoderBinary, rootFlags, flags, coderdConfig.HostnamePrefix,
+				))
+			}
 
-					// Finally, add the standard options.
-					err := configOptions.addOptions(defaultOptions...)
-					if err != nil {
-						return err
-					}
+			// Create a copy of the options so we can modify them.
+			configOptions := sshConfigOpts
+			configOptions.sshOptions = nil
 
-					hostBlock := []string{
-						"Host " + sshHostname,
-					}
-					// Prefix with '\t'
-					for _, v := range configOptions.sshOptions {
-						hostBlock = append(hostBlock, "\t"+v)
-					}
+			// User options first (SSH only uses the first
+			// option unless it can be given multiple times)
+			for _, opt := range sshConfigOpts.sshOptions {
+				err := configOptions.addOptions(opt)
+				if err != nil {
+					return xerrors.Errorf("add flag config option %q: %w", opt, err)
+				}
+			}
 
-					_, _ = buf.WriteString(strings.Join(hostBlock, "\n"))
-					_ = buf.WriteByte('\n')
+			// Deployment options second, allow them to
+			// override standard options.
+			for k, v := range coderdConfig.SSHConfigOptions {
+				opt := fmt.Sprintf("%s %s", k, v)
+				err := configOptions.addOptions(opt)
+				if err != nil {
+					return xerrors.Errorf("add coderd config option %q: %w", opt, err)
 				}
 			}
 
+			// Finally, add the standard options.
+			if err := configOptions.addOptions(defaultOptions...); err != nil {
+				return err
+			}
+
+			hostBlock := []string{
+				"Host " + coderdConfig.HostnamePrefix + "*",
+			}
+			// Prefix with '\t'
+			for _, v := range configOptions.sshOptions {
+				hostBlock = append(hostBlock, "\t"+v)
+			}
+
+			_, _ = buf.WriteString(strings.Join(hostBlock, "\n"))
+			_ = buf.WriteByte('\n')
+
 			sshConfigWriteSectionEnd(buf)
 
 			// Write the remainder of the users config file to buf.
@@ -532,9 +441,17 @@ func (r *RootCmd) configSSH() *serpent.Command {
 				_, _ = fmt.Fprintf(out, "Updated %q\n", sshConfigFile)
 			}
 
-			if len(workspaceConfigs) > 0 {
+			res, err := client.Workspaces(ctx, codersdk.WorkspaceFilter{
+				Owner: codersdk.Me,
+				Limit: 1,
+			})
+			if err != nil {
+				return xerrors.Errorf("fetch workspaces failed: %w", err)
+			}
+
+			if len(res.Workspaces) > 0 {
 				_, _ = fmt.Fprintln(out, "You should now be able to ssh into your workspace.")
-				_, _ = fmt.Fprintf(out, "For example, try running:\n\n\t$ ssh %s%s\n", coderdConfig.HostnamePrefix, workspaceConfigs[0].Name)
+				_, _ = fmt.Fprintf(out, "For example, try running:\n\n\t$ ssh %s%s\n", coderdConfig.HostnamePrefix, res.Workspaces[0].Name)
 			} else {
 				_, _ = fmt.Fprint(out, "You don't have any workspaces yet, try creating one with:\n\n\t$ coder create <workspace>\n")
 			}
diff --git a/cli/configssh_test.go b/cli/configssh_test.go
index 5bedd18cb27dc..3b88ab1e54db7 100644
--- a/cli/configssh_test.go
+++ b/cli/configssh_test.go
@@ -1,8 +1,6 @@
 package cli_test
 
 import (
-	"bufio"
-	"bytes"
 	"context"
 	"fmt"
 	"io"
@@ -16,7 +14,6 @@ import (
 	"sync"
 	"testing"
 
-	"github.com/google/uuid"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 
@@ -27,7 +24,6 @@ import (
 	"github.com/coder/coder/v2/coderd/database/dbfake"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/codersdk/workspacesdk"
-	"github.com/coder/coder/v2/provisionersdk/proto"
 	"github.com/coder/coder/v2/pty/ptytest"
 	"github.com/coder/coder/v2/testutil"
 )
@@ -194,7 +190,7 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 		ssh string
 	}
 	type wantConfig struct {
-		ssh        string
+		ssh        []string
 		regexMatch string
 	}
 	type match struct {
@@ -215,10 +211,10 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 				{match: "Continue?", write: "yes"},
 			},
 			wantConfig: wantConfig{
-				ssh: strings.Join([]string{
-					baseHeader,
-					"",
-				}, "\n"),
+				ssh: []string{
+					headerStart,
+					headerEnd,
+				},
 			},
 		},
 		{
@@ -230,44 +226,19 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 				}, "\n"),
 			},
 			wantConfig: wantConfig{
-				ssh: strings.Join([]string{
-					"Host myhost",
-					"	HostName myhost",
-					baseHeader,
-					"",
-				}, "\n"),
+				ssh: []string{
+					strings.Join([]string{
+						"Host myhost",
+						"	HostName myhost",
+					}, "\n"),
+					headerStart,
+					headerEnd,
+				},
 			},
 			matches: []match{
 				{match: "Continue?", write: "yes"},
 			},
 		},
-		{
-			name: "Section is not moved on re-run",
-			writeConfig: writeConfig{
-				ssh: strings.Join([]string{
-					"Host myhost",
-					"	HostName myhost",
-					"",
-					baseHeader,
-					"",
-					"Host otherhost",
-					"	HostName otherhost",
-					"",
-				}, "\n"),
-			},
-			wantConfig: wantConfig{
-				ssh: strings.Join([]string{
-					"Host myhost",
-					"	HostName myhost",
-					"",
-					baseHeader,
-					"",
-					"Host otherhost",
-					"	HostName otherhost",
-					"",
-				}, "\n"),
-			},
-		},
 		{
 			name: "Section is not moved on re-run with new options",
 			writeConfig: writeConfig{
@@ -283,20 +254,24 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 				}, "\n"),
 			},
 			wantConfig: wantConfig{
-				ssh: strings.Join([]string{
-					"Host myhost",
-					"	HostName myhost",
-					"",
-					headerStart,
-					"# Last config-ssh options:",
-					"# :ssh-option=ForwardAgent=yes",
-					"#",
-					headerEnd,
-					"",
-					"Host otherhost",
-					"	HostName otherhost",
-					"",
-				}, "\n"),
+				ssh: []string{
+					strings.Join([]string{
+						"Host myhost",
+						"	HostName myhost",
+						"",
+						headerStart,
+						"# Last config-ssh options:",
+						"# :ssh-option=ForwardAgent=yes",
+						"#",
+					}, "\n"),
+					strings.Join([]string{
+						headerEnd,
+						"",
+						"Host otherhost",
+						"	HostName otherhost",
+						"",
+					}, "\n"),
+				},
 			},
 			args: []string{
 				"--ssh-option", "ForwardAgent=yes",
@@ -314,10 +289,13 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 				}, "\n"),
 			},
 			wantConfig: wantConfig{
-				ssh: strings.Join([]string{
-					baseHeader,
-					"",
-				}, "\n"),
+				ssh: []string{
+					headerStart,
+					strings.Join([]string{
+						headerEnd,
+						"",
+					}, "\n"),
+				},
 			},
 			matches: []match{
 				{match: "Continue?", write: "yes"},
@@ -329,14 +307,17 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 				ssh: "",
 			},
 			wantConfig: wantConfig{
-				ssh: strings.Join([]string{
-					headerStart,
-					"# Last config-ssh options:",
-					"# :ssh-option=ForwardAgent=yes",
-					"#",
-					headerEnd,
-					"",
-				}, "\n"),
+				ssh: []string{
+					strings.Join([]string{
+						headerStart,
+						"# Last config-ssh options:",
+						"# :ssh-option=ForwardAgent=yes",
+						"#",
+					}, "\n"),
+					strings.Join([]string{
+						headerEnd,
+						"",
+					}, "\n")},
 			},
 			args: []string{"--ssh-option", "ForwardAgent=yes"},
 			matches: []match{
@@ -351,14 +332,17 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 				}, "\n"),
 			},
 			wantConfig: wantConfig{
-				ssh: strings.Join([]string{
-					headerStart,
-					"# Last config-ssh options:",
-					"# :ssh-option=ForwardAgent=yes",
-					"#",
-					headerEnd,
-					"",
-				}, "\n"),
+				ssh: []string{
+					strings.Join([]string{
+						headerStart,
+						"# Last config-ssh options:",
+						"# :ssh-option=ForwardAgent=yes",
+						"#",
+					}, "\n"),
+					strings.Join([]string{
+						headerEnd,
+						"",
+					}, "\n")},
 			},
 			args: []string{"--ssh-option", "ForwardAgent=yes"},
 			matches: []match{
@@ -378,40 +362,19 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 				}, "\n"),
 			},
 			wantConfig: wantConfig{
-				ssh: strings.Join([]string{
-					baseHeader,
-					"",
-				}, "\n"),
+				ssh: []string{
+					headerStart,
+					strings.Join([]string{
+						headerEnd,
+						"",
+					}, "\n"),
+				},
 			},
 			matches: []match{
 				{match: "Use new options?", write: "yes"},
 				{match: "Continue?", write: "yes"},
 			},
 		},
-		{
-			name: "No prompt on no changes",
-			writeConfig: writeConfig{
-				ssh: strings.Join([]string{
-					headerStart,
-					"# Last config-ssh options:",
-					"# :ssh-option=ForwardAgent=yes",
-					"#",
-					headerEnd,
-					"",
-				}, "\n"),
-			},
-			wantConfig: wantConfig{
-				ssh: strings.Join([]string{
-					headerStart,
-					"# Last config-ssh options:",
-					"# :ssh-option=ForwardAgent=yes",
-					"#",
-					headerEnd,
-					"",
-				}, "\n"),
-			},
-			args: []string{"--ssh-option", "ForwardAgent=yes"},
-		},
 		{
 			name: "No changes when continue = no",
 			writeConfig: writeConfig{
@@ -425,14 +388,14 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 				}, "\n"),
 			},
 			wantConfig: wantConfig{
-				ssh: strings.Join([]string{
+				ssh: []string{strings.Join([]string{
 					headerStart,
 					"# Last config-ssh options:",
 					"# :ssh-option=ForwardAgent=yes",
 					"#",
 					headerEnd,
 					"",
-				}, "\n"),
+				}, "\n")},
 			},
 			args: []string{"--ssh-option", "ForwardAgent=no"},
 			matches: []match{
@@ -453,29 +416,32 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 				}, "\n"),
 			},
 			wantConfig: wantConfig{
-				ssh: strings.Join([]string{
-					// Last options overwritten.
-					baseHeader,
-					"",
-				}, "\n"),
+				ssh: []string{
+					headerStart,
+					headerEnd,
+				},
 			},
 			args: []string{"--yes"},
 		},
 		{
 			name: "Serialize supported flags",
 			wantConfig: wantConfig{
-				ssh: strings.Join([]string{
-					headerStart,
-					"# Last config-ssh options:",
-					"# :wait=yes",
-					"# :ssh-host-prefix=coder-test.",
-					"# :header=X-Test-Header=foo",
-					"# :header=X-Test-Header2=bar",
-					"# :header-command=printf h1=v1 h2=\"v2\" h3='v3'",
-					"#",
-					headerEnd,
-					"",
-				}, "\n"),
+				ssh: []string{
+					strings.Join([]string{
+						headerStart,
+						"# Last config-ssh options:",
+						"# :wait=yes",
+						"# :ssh-host-prefix=coder-test.",
+						"# :header=X-Test-Header=foo",
+						"# :header=X-Test-Header2=bar",
+						"# :header-command=printf h1=v1 h2=\"v2\" h3='v3'",
+						"#",
+					}, "\n"),
+					strings.Join([]string{
+						headerEnd,
+						"",
+					}, "\n"),
+				},
 			},
 			args: []string{
 				"--yes",
@@ -500,15 +466,20 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 				}, "\n"),
 			},
 			wantConfig: wantConfig{
-				ssh: strings.Join([]string{
-					headerStart,
-					"# Last config-ssh options:",
-					"# :wait=no",
-					"# :ssh-option=ForwardAgent=yes",
-					"#",
-					headerEnd,
-					"",
-				}, "\n"),
+				ssh: []string{
+					strings.Join(
+						[]string{
+							headerStart,
+							"# Last config-ssh options:",
+							"# :wait=no",
+							"# :ssh-option=ForwardAgent=yes",
+							"#",
+						}, "\n"),
+					strings.Join([]string{
+						headerEnd,
+						"",
+					}, "\n"),
+				},
 			},
 			args: []string{
 				"--use-previous-options",
@@ -524,10 +495,10 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 				}, "\n"),
 			},
 			wantConfig: wantConfig{
-				ssh: strings.Join([]string{
+				ssh: []string{strings.Join([]string{
 					baseHeader,
 					"",
-				}, "\n"),
+				}, "\n")},
 			},
 			args: []string{
 				"--ssh-option", "ForwardAgent=yes",
@@ -586,7 +557,7 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 			wantErr:  false,
 			hasAgent: true,
 			wantConfig: wantConfig{
-				regexMatch: `ProxyCommand .* --header "X-Test-Header=foo" --header "X-Test-Header2=bar" ssh`,
+				regexMatch: `ProxyCommand .* --header "X-Test-Header=foo" --header "X-Test-Header2=bar" ssh .* --ssh-host-prefix coder. %h`,
 			},
 		},
 		{
@@ -598,7 +569,7 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 			wantErr:  false,
 			hasAgent: true,
 			wantConfig: wantConfig{
-				regexMatch: `ProxyCommand .* --header-command "printf h1=v1" ssh`,
+				regexMatch: `ProxyCommand .* --header-command "printf h1=v1" ssh .* --ssh-host-prefix coder. %h`,
 			},
 		},
 		{
@@ -610,7 +581,7 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 			wantErr:  false,
 			hasAgent: true,
 			wantConfig: wantConfig{
-				regexMatch: `ProxyCommand .* --header-command "printf h1=v1 h2=\\\"v2\\\"" ssh`,
+				regexMatch: `ProxyCommand .* --header-command "printf h1=v1 h2=\\\"v2\\\"" ssh .* --ssh-host-prefix coder. %h`,
 			},
 		},
 		{
@@ -622,7 +593,7 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 			wantErr:  false,
 			hasAgent: true,
 			wantConfig: wantConfig{
-				regexMatch: `ProxyCommand .* --header-command "printf h1=v1 h2='v2'" ssh`,
+				regexMatch: `ProxyCommand .* --header-command "printf h1=v1 h2='v2'" ssh .* --ssh-host-prefix coder. %h`,
 			},
 		},
 		{
@@ -686,10 +657,15 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 
 			<-done
 
-			if tt.wantConfig.ssh != "" || tt.wantConfig.regexMatch != "" {
+			if len(tt.wantConfig.ssh) != 0 || tt.wantConfig.regexMatch != "" {
 				got := sshConfigFileRead(t, sshConfigName)
-				if tt.wantConfig.ssh != "" {
-					assert.Equal(t, tt.wantConfig.ssh, got)
+				// Require that the generated config has the expected snippets in order.
+				for _, want := range tt.wantConfig.ssh {
+					idx := strings.Index(got, want)
+					if idx == -1 {
+						require.Contains(t, got, want)
+					}
+					got = got[idx+len(want):]
 				}
 				if tt.wantConfig.regexMatch != "" {
 					assert.Regexp(t, tt.wantConfig.regexMatch, got, "regex match")
@@ -698,135 +674,3 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 		})
 	}
 }
-
-func TestConfigSSH_Hostnames(t *testing.T) {
-	t.Parallel()
-
-	type resourceSpec struct {
-		name   string
-		agents []string
-	}
-	tests := []struct {
-		name      string
-		resources []resourceSpec
-		expected  []string
-	}{
-		{
-			name: "one resource with one agent",
-			resources: []resourceSpec{
-				{name: "foo", agents: []string{"agent1"}},
-			},
-			expected: []string{"coder.@", "coder.@.agent1"},
-		},
-		{
-			name: "one resource with two agents",
-			resources: []resourceSpec{
-				{name: "foo", agents: []string{"agent1", "agent2"}},
-			},
-			expected: []string{"coder.@.agent1", "coder.@.agent2"},
-		},
-		{
-			name: "two resources with one agent",
-			resources: []resourceSpec{
-				{name: "foo", agents: []string{"agent1"}},
-				{name: "bar"},
-			},
-			expected: []string{"coder.@", "coder.@.agent1"},
-		},
-		{
-			name: "two resources with two agents",
-			resources: []resourceSpec{
-				{name: "foo", agents: []string{"agent1"}},
-				{name: "bar", agents: []string{"agent2"}},
-			},
-			expected: []string{"coder.@.agent1", "coder.@.agent2"},
-		},
-	}
-
-	for _, tt := range tests {
-		tt := tt
-		t.Run(tt.name, func(t *testing.T) {
-			t.Parallel()
-
-			var resources []*proto.Resource
-			for _, resourceSpec := range tt.resources {
-				resource := &proto.Resource{
-					Name: resourceSpec.name,
-					Type: "aws_instance",
-				}
-				for _, agentName := range resourceSpec.agents {
-					resource.Agents = append(resource.Agents, &proto.Agent{
-						Id:   uuid.NewString(),
-						Name: agentName,
-					})
-				}
-				resources = append(resources, resource)
-			}
-
-			client, db := coderdtest.NewWithDatabase(t, nil)
-			owner := coderdtest.CreateFirstUser(t, client)
-			member, memberUser := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
-
-			r := dbfake.WorkspaceBuild(t, db, database.WorkspaceTable{
-				OrganizationID: owner.OrganizationID,
-				OwnerID:        memberUser.ID,
-			}).Resource(resources...).Do()
-			sshConfigFile := sshConfigFileName(t)
-
-			inv, root := clitest.New(t, "config-ssh", "--ssh-config-file", sshConfigFile)
-			clitest.SetupConfig(t, member, root)
-
-			pty := ptytest.New(t)
-			inv.Stdin = pty.Input()
-			inv.Stdout = pty.Output()
-			clitest.Start(t, inv)
-
-			matches := []struct {
-				match, write string
-			}{
-				{match: "Continue?", write: "yes"},
-			}
-			for _, m := range matches {
-				pty.ExpectMatch(m.match)
-				pty.WriteLine(m.write)
-			}
-
-			pty.ExpectMatch("Updated")
-
-			var expectedHosts []string
-			for _, hostnamePattern := range tt.expected {
-				hostname := strings.ReplaceAll(hostnamePattern, "@", r.Workspace.Name)
-				expectedHosts = append(expectedHosts, hostname)
-			}
-
-			hosts := sshConfigFileParseHosts(t, sshConfigFile)
-			require.ElementsMatch(t, expectedHosts, hosts)
-		})
-	}
-}
-
-// sshConfigFileParseHosts reads a file in the format of .ssh/config and extracts
-// the hostnames that are listed in "Host" directives.
-func sshConfigFileParseHosts(t *testing.T, name string) []string {
-	t.Helper()
-	b, err := os.ReadFile(name)
-	require.NoError(t, err)
-
-	var result []string
-	lineScanner := bufio.NewScanner(bytes.NewBuffer(b))
-	for lineScanner.Scan() {
-		line := lineScanner.Text()
-		line = strings.TrimSpace(line)
-
-		tokenScanner := bufio.NewScanner(bytes.NewBufferString(line))
-		tokenScanner.Split(bufio.ScanWords)
-		ok := tokenScanner.Scan()
-		if ok && tokenScanner.Text() == "Host" {
-			for tokenScanner.Scan() {
-				result = append(result, tokenScanner.Text())
-			}
-		}
-	}
-
-	return result
-}