diff --git a/src/main/ssh/ssh-connection.test.ts b/src/main/ssh/ssh-connection.test.ts
index f40d27077a8..8a35c3d42aa 100644
--- a/src/main/ssh/ssh-connection.test.ts
+++ b/src/main/ssh/ssh-connection.test.ts
@@ -22,6 +22,7 @@ type MockSshClient = {
   _sock: Socket | undefined
   lastExecCommand?: string
   lastConnectConfig?: unknown
+  exec: (cmd: string, cb: (err: Error | undefined, channel: unknown) => void) => void
 }
 let clientInstances: MockSshClient[] = []
 
@@ -707,6 +708,84 @@ describe('SshConnection', () => {
     }
   })
 
+  it('retries a session-limit-refused exec open and succeeds on a later attempt', async () => {
+    const conn = new SshConnection(createTarget(), createCallbacks())
+    await conn.connect()
+    const channel = { close: vi.fn() }
+    const execMock = vi
+      .fn<(cmd: string, cb: (err: Error | undefined, ch: unknown) => void) => void>()
+      .mockImplementationOnce((_cmd, cb) => {
+        cb(
+          Object.assign(new Error('(SSH) Channel open failure: open failed'), { reason: 2 }),
+          undefined
+        )
+      })
+      .mockImplementation((_cmd, cb) => cb(undefined, channel))
+    clientInstances[0].exec = execMock as never
+
+    await expect(conn.exec('printf ready')).resolves.toBe(channel)
+    expect(execMock).toHaveBeenCalledTimes(2)
+  })
+
+  it('surfaces the session-limit error once open retries are exhausted', async () => {
+    const conn = new SshConnection(createTarget(), createCallbacks())
+    await conn.connect()
+    const refusal = Object.assign(new Error('(SSH) Channel open failure: open failed'), {
+      reason: 2
+    })
+    const execMock = vi
+      .fn<(cmd: string, cb: (err: Error | undefined, ch: unknown) => void) => void>()
+      .mockImplementation((_cmd, cb) => cb(refusal, undefined))
+    clientInstances[0].exec = execMock as never
+
+    await expect(conn.exec('printf ready')).rejects.toBe(refusal)
+    expect(execMock).toHaveBeenCalledTimes(4)
+  })
+
+  it('does not retry non-session-limit exec open failures', async () => {
+    const conn = new SshConnection(createTarget(), createCallbacks())
+    await conn.connect()
+    const failure = new Error('Not connected')
+    const execMock = vi
+      .fn<(cmd: string, cb: (err: Error | undefined, ch: unknown) => void) => void>()
+      .mockImplementation((_cmd, cb) => cb(failure, undefined))
+    clientInstances[0].exec = execMock as never
+
+    await expect(conn.exec('printf ready')).rejects.toBe(failure)
+    expect(execMock).toHaveBeenCalledTimes(1)
+  })
+
+  it('settles an abort during channel open only after the late channel closes', async () => {
+    const conn = new SshConnection(createTarget(), createCallbacks())
+    await conn.connect()
+    execBehavior = 'pending'
+    const controller = new AbortController()
+    const lateChannel = Object.assign(new EventEmitter(), {
+      close: vi.fn(),
+      resume: vi.fn(),
+      stderr: { resume: vi.fn() }
+    })
+
+    const outcomePromise = conn
+      .exec('printf ready', { signal: controller.signal })
+      .then(() => 'opened')
+      .catch((error: Error) => error.name)
+
+    await Promise.resolve()
+    controller.abort()
+    pendingExecCallback?.(undefined, lateChannel)
+
+    // Why: the sshd session slot is freed only when the channel finishes
+    // closing — settling before 'close' lets the next open race the close.
+    const early = await Promise.race([outcomePromise, Promise.resolve('pending')])
+    expect(early).toBe('pending')
+    expect(lateChannel.close).toHaveBeenCalledTimes(1)
+    expect(lateChannel.resume).toHaveBeenCalled()
+
+    lateChannel.emit('close')
+    await expect(outcomePromise).resolves.toBe('AbortError')
+  })
+
   it('times out when ssh2 never opens an SFTP channel', async () => {
     const conn = new SshConnection(createTarget(), createCallbacks())
     await conn.connect()
diff --git a/src/main/ssh/ssh-connection.ts b/src/main/ssh/ssh-connection.ts
index 528f03c4c58..73858c99c2d 100644
--- a/src/main/ssh/ssh-connection.ts
+++ b/src/main/ssh/ssh-connection.ts
@@ -35,12 +35,24 @@ import {
   type SshConnectionCallbacks
 } from './ssh-connection-utils'
 import type { RemoteHostPlatform } from './ssh-remote-platform'
+import { isSshSessionLimitError } from './ssh-session-limit-error'
 export type { SshConnectionCallbacks } from './ssh-connection-utils'
 
 type SshRemoteFileOptions = {
   hostPlatform?: RemoteHostPlatform
 }
 
+// Upper bound on waiting for an aborted late-opened channel to finish closing
+// before rejecting anyway. Normal closes complete in one network round-trip.
+const ABORTED_CHANNEL_CLOSE_GRACE_MS = 5_000
+
+// Why: on session-limited servers (MaxSessions), a channel open can be refused
+// transiently — e.g. our next CHANNEL_OPEN reaching sshd a few microseconds
+// before it finishes processing the previous channel's close. A refused open
+// never started the command, so retrying is always safe.
+const SESSION_LIMIT_OPEN_RETRIES = 4
+const SESSION_LIMIT_OPEN_RETRY_DELAY_MS = 150
+
 function cloneResolvedConfig(config: SshResolvedConfig | null): SshResolvedConfig | null {
   if (!config) {
     return null
@@ -132,10 +144,14 @@ export class SshConnection {
     }
     const client = this.client
     const remoteCommand = options?.wrapCommand === false ? cmd : wrapRemoteCommandForPosixShell(cmd)
-    return this.waitForSshCallback(
-      'SSH exec channel timed out',
-      (callback) => client.exec(remoteCommand, callback),
-      (channel) => channel.close(),
+    return this.openSessionChannelWithRetry(
+      () =>
+        this.waitForSshCallback(
+          'SSH exec channel timed out',
+          (callback) => client.exec(remoteCommand, callback),
+          (channel) => channel.close(),
+          options?.signal
+        ),
       options?.signal
     )
   }
@@ -148,13 +164,39 @@ export class SshConnection {
       throw new Error('Not connected')
     }
     const client = this.client
-    return this.waitForSshCallback(
-      'SSH SFTP channel timed out',
-      (callback) => client.sftp(callback),
-      (sftp) => sftp.end()
+    return this.openSessionChannelWithRetry(() =>
+      this.waitForSshCallback(
+        'SSH SFTP channel timed out',
+        (callback) => client.sftp(callback),
+        (sftp) => sftp.end()
+      )
     )
   }
 
+  private async openSessionChannelWithRetry<T>(
+    open: () => Promise<T>,
+    signal?: AbortSignal
+  ): Promise<T> {
+    let lastError: unknown
+    for (let attempt = 0; attempt < SESSION_LIMIT_OPEN_RETRIES; attempt++) {
+      if (attempt > 0) {
+        await new Promise((resolve) => setTimeout(resolve, SESSION_LIMIT_OPEN_RETRY_DELAY_MS))
+        if (signal?.aborted) {
+          throw createSshOperationAbortError()
+        }
+      }
+      try {
+        return await open()
+      } catch (err) {
+        if (!isSshSessionLimitError(err)) {
+          throw err
+        }
+        lastError = err
+      }
+    }
+    throw lastError
+  }
+
   private waitForSshCallback<T>(
     timeoutMessage: string,
     register: (callback: (error: Error | undefined, value: T) => void) => void,
@@ -163,23 +205,57 @@ export class SshConnection {
   ): Promise<T> {
     return new Promise((resolve, reject) => {
       let settled = false
+      // Why: rejecting the instant the signal aborts lets the caller proceed
+      // while the in-flight channel open completes in the background and holds
+      // a server-side session slot (MaxSessions). Mark the abort and settle
+      // from the open callback, after the late resource has been closed.
+      let abortRequested = false
       const cleanup = (): void => {
         clearTimeout(timer)
         signal?.removeEventListener('abort', onAbort)
       }
       const onAbort = (): void => {
-        if (settled) {
-          return
-        }
-        settled = true
-        cleanup()
-        reject(createSshOperationAbortError())
+        abortRequested = true
       }
       const timer = setTimeout(() => {
         settled = true
         signal?.removeEventListener('abort', onAbort)
-        reject(new Error(timeoutMessage))
+        reject(abortRequested ? createSshOperationAbortError() : new Error(timeoutMessage))
       }, CONNECT_TIMEOUT_MS)
+      const rejectAfterClose = (value: T): void => {
+        const abortError = createSshOperationAbortError()
+        const emitter = value as Partial<NodeJS.EventEmitter> & {
+          resume?: () => void
+          stderr?: { resume?: () => void }
+        }
+        let finished = false
+        const done = (): void => {
+          if (finished) {
+            return
+          }
+          finished = true
+          clearTimeout(closeGraceTimer)
+          reject(abortError)
+        }
+        // Why: bounded — a remote that never confirms the close must not hang
+        // the aborted operation forever.
+        const closeGraceTimer = setTimeout(done, ABORTED_CHANNEL_CLOSE_GRACE_MS)
+        if (typeof emitter.once === 'function') {
+          emitter.once('close', done)
+        }
+        // Why: ssh2 withholds the 'close' event until the channel's streams
+        // are drained; nobody else will ever read this discarded channel.
+        emitter.resume?.()
+        emitter.stderr?.resume?.()
+        try {
+          cleanupLateValue?.(value)
+        } catch {
+          /* best effort */
+        }
+        if (typeof emitter.once !== 'function') {
+          done()
+        }
+      }
       const finish = (error: Error | undefined, value?: T): void => {
         if (settled) {
           // Why: ssh2 can invoke the open callback after our timeout has
@@ -196,6 +272,14 @@ export class SshConnection {
         }
         settled = true
         cleanup()
+        if (abortRequested) {
+          if (!error && value !== undefined) {
+            rejectAfterClose(value)
+          } else {
+            reject(createSshOperationAbortError())
+          }
+          return
+        }
         if (error) {
           reject(error)
           return
@@ -203,7 +287,9 @@ export class SshConnection {
         resolve(value as T)
       }
       if (signal?.aborted) {
-        onAbort()
+        // No open is in flight yet, so failing fast leaks nothing.
+        cleanup()
+        reject(createSshOperationAbortError())
         return
       }
       signal?.addEventListener('abort', onAbort, { once: true })
diff --git a/src/main/ssh/ssh-relay-deploy-helpers.test.ts b/src/main/ssh/ssh-relay-deploy-helpers.test.ts
index 8bd40901dae..c2d762b261b 100644
--- a/src/main/ssh/ssh-relay-deploy-helpers.test.ts
+++ b/src/main/ssh/ssh-relay-deploy-helpers.test.ts
@@ -230,8 +230,22 @@ describe('execCommand', () => {
     await Promise.resolve()
     controller.abort()
 
-    await expect(commandPromise).rejects.toMatchObject({ name: 'AbortError' })
+    // Why: sshd frees the MaxSessions slot only when the channel finishes
+    // closing, so abort must request close and settle from the 'close' event —
+    // settling immediately lets the sequential fallback race the closing
+    // channel and get refused.
     expect(channel.close).toHaveBeenCalledOnce()
+    const settledEarly = await Promise.race([
+      commandPromise.then(
+        () => 'settled',
+        () => 'settled'
+      ),
+      Promise.resolve('pending')
+    ])
+    expect(settledEarly).toBe('pending')
+    channel.emit('close', 0)
+
+    await expect(commandPromise).rejects.toMatchObject({ name: 'AbortError' })
     expect(channel.listenerCount('error')).toBe(0)
     expect(channel.listenerCount('data')).toBe(0)
     expect(channel.listenerCount('close')).toBe(0)
@@ -257,8 +271,13 @@ describe('execCommand', () => {
     controller.abort()
     resolveExec(channel)
 
-    await expect(commandPromise).rejects.toMatchObject({ name: 'AbortError' })
+    await Promise.resolve()
+    await Promise.resolve()
     expect(channel.close).toHaveBeenCalledOnce()
+    // Nonzero exit from the killed command must still surface as AbortError.
+    channel.emit('close', 1)
+
+    await expect(commandPromise).rejects.toMatchObject({ name: 'AbortError' })
     expect(channel.listenerCount('error')).toBe(0)
     expect(channel.listenerCount('data')).toBe(0)
     expect(channel.listenerCount('close')).toBe(0)
diff --git a/src/main/ssh/ssh-relay-deploy-helpers.ts b/src/main/ssh/ssh-relay-deploy-helpers.ts
index 1473e3233cd..4abeb29a61a 100644
--- a/src/main/ssh/ssh-relay-deploy-helpers.ts
+++ b/src/main/ssh/ssh-relay-deploy-helpers.ts
@@ -275,11 +275,16 @@ export async function execCommand(
       fn(val as never)
     }
     const fail = (err: Error): void => {
-      settle(reject, err)
+      settle(reject, abortRequested ? createSshOperationAbortError() : err)
     }
+    // Why: sshd counts the session against MaxSessions until CHANNEL_CLOSE
+    // completes. Settling on abort before the channel actually closes lets the
+    // concurrent-bootstrap sequential fallback reissue an exec while the slot
+    // is still held, so it gets refused again. Close and settle from onClose.
+    let abortRequested = false
     const onAbort = (): void => {
+      abortRequested = true
       channel.close()
-      settle(reject, createSshOperationAbortError())
     }
     const onStdoutData = (data: Buffer): void => {
       stdout += data.toString('utf-8')
@@ -288,7 +293,9 @@ export async function execCommand(
       stderr += data.toString('utf-8')
     }
     const onClose = (code: number): void => {
-      if (code !== 0) {
+      if (abortRequested) {
+        settle(reject, createSshOperationAbortError())
+      } else if (code !== 0) {
         const output = stderr.trim() || stdout.trim()
         settle(reject, new Error(`Command "${command}" failed (exit ${code}): ${output}`))
       } else {
@@ -297,7 +304,12 @@ export async function execCommand(
     }
     const timeout = setTimeout(() => {
       channel.close()
-      settle(reject, new Error(`Command "${command}" timed out after ${timeoutMs / 1000}s`))
+      settle(
+        reject,
+        abortRequested
+          ? createSshOperationAbortError()
+          : new Error(`Command "${command}" timed out after ${timeoutMs / 1000}s`)
+      )
     }, timeoutMs)
 
     // Why: remote reboot tears down exec channels with stream errors. Without
diff --git a/src/main/ssh/ssh-relay-session.ts b/src/main/ssh/ssh-relay-session.ts
index b078db39760..58bf3fbf798 100644
--- a/src/main/ssh/ssh-relay-session.ts
+++ b/src/main/ssh/ssh-relay-session.ts
@@ -531,7 +531,19 @@ export class SshRelaySession {
       return false
     }
 
-    await this.installRemoteOrcaCliShim()
+    try {
+      await this.installRemoteOrcaCliShim()
+    } catch (error) {
+      // Why: the remote `orca` CLI shim is a convenience bridge. On session-
+      // limited remotes (MaxSessions=1) the relay bridge holds the only slot,
+      // so this raw-connection install can fail — that must not fail the
+      // whole connection, matching the managed-hook install above.
+      console.warn(
+        `[ssh-relay-session] remote orca CLI shim install failed for ${this.targetId}: ${
+          error instanceof Error ? error.message : String(error)
+        }`
+      )
+    }
     if (shouldContinue && !shouldContinue()) {
       return false
     }
diff --git a/src/main/ssh/ssh-session-limit-error.test.ts b/src/main/ssh/ssh-session-limit-error.test.ts
index a2aaac5e4b3..65608fd9a6e 100644
--- a/src/main/ssh/ssh-session-limit-error.test.ts
+++ b/src/main/ssh/ssh-session-limit-error.test.ts
@@ -10,6 +10,16 @@ describe('isSshSessionLimitError', () => {
     ).toBe(true)
   })
 
+  it('matches the OpenSSH MaxSessions rejection (SSH2_OPEN_CONNECT_FAILED + "open failed")', () => {
+    // Why: stock OpenSSH sshd refuses session channels over MaxSessions with
+    // reason 2, not resource-shortage — observed against OpenSSH 9.2.
+    expect(
+      isSshSessionLimitError(
+        Object.assign(new Error('(SSH) Channel open failure: open failed'), { reason: 2 })
+      )
+    ).toBe(true)
+  })
+
   it('matches OpenSSH mux and MaxSessions failures', () => {
     expect(
       isSshSessionLimitError(
@@ -29,11 +39,6 @@ describe('isSshSessionLimitError', () => {
         Object.assign(new Error('(SSH) Channel open failure: open failed'), { reason: 1 })
       )
     ).toBe(false)
-    expect(
-      isSshSessionLimitError(
-        Object.assign(new Error('(SSH) Channel open failure: open failed'), { reason: 2 })
-      )
-    ).toBe(false)
     expect(
       isSshSessionLimitError(
         Object.assign(new Error('(SSH) Channel open failure: open failed'), { reason: 3 })
diff --git a/src/main/ssh/ssh-session-limit-error.ts b/src/main/ssh/ssh-session-limit-error.ts
index aed848525b8..d3f1c120b11 100644
--- a/src/main/ssh/ssh-session-limit-error.ts
+++ b/src/main/ssh/ssh-session-limit-error.ts
@@ -4,8 +4,11 @@ export function isSshSessionLimitError(err: unknown): boolean {
   }
   const reason = (err as { reason?: unknown }).reason
   const message = err.message.toLowerCase()
+  // Why: OpenSSH rejects session channels over MaxSessions with
+  // SSH2_OPEN_CONNECT_FAILED (2) and the literal description "open failed";
+  // reason 4 (resource shortage) covers other server implementations.
   if (
-    reason === 4 &&
+    (reason === 2 || reason === 4) &&
     (message.includes('channel open failure') || message.includes('open failed'))
   ) {
     return true