A federal judge today questioned Alabama Department of Corrections officials about its procedures for lethal injection executions, which have been problematic, and about what he said was the “moving target” for Alabama to develop an alternative method of execution by nitrogen hypoxia.

U.S. District Judge R. Austin Huffaker Jr., held an hour and 40-minute hearing in the case of Kenneth Eugene Smith, who is asking the court to block his execution by lethal injection, set for Nov. 17 at Holman Correctional Facility in Atmore.

Huffaker heard arguments and questioned lawyers for Smith and for the state. He did not rule on the state’s motion to dismiss Smith’s lawsuit. Lawyers for the state say Smith waited too late to file his lawsuit and that his case lacks substance because it is general challenge to the established practice of lethal injection.

Smith was sent to death row in 1996 after his conviction in the murder-for-hire killing of Elizabeth Dorlene Sennett, a 45-year-old grandmother and pastor’s wife who was killed in March 1988 in her home in north Alabama. Her husband paid to have her killed.

Smith’s lawyer, Robert Grass, told the judge the state’s lethal injection procedure carries an intolerable risk of violating the 8th Amendment prohibition on cruel and unusual punishment. Smith’s lawsuit cites the execution of Joe Nathan James Jr. in July, which took several hours to carry out and has been labeled as “botched” by some death penalty opponents. Smith also cites the failed execution of Alan Eugene Miller, which the ADOC called off on Sept. 22 after failure to tap a vein to administer the lethal drugs and a three-hour delay resulting from Miller’s effort to block the execution in federal court. Miller has claimed in his lawsuit that he was poked with needles for 90 minutes. Alabama also called off the execution of Doyle Hamm in 2018 because of failure to find a vein.

Grass told Huffaker that Smith’s lawyers would like to take depositions from the team at ADOC that established the IV connection to execute James in July. A doctor who examined James’ body in a private autopsy said there was evidence of a “cutdown” procedure on James’ arm, an incision made to expose a vein. Assistant Attorney General Richard Anderson, representing the ADOC, said in court today that no “cutdown” procedure was performed on James and acknowledged that would be outside the execution protocol. The state had previously said in a court filing that there was no “cutdown” done on James. Anderson also told Huffaker that James was not given an intramuscular sedative before the execution was carried out. Some have speculated that James was sedated because he did not appear to be responsive during the time the media and witnesses were allowed to watch the execution.

The state agreed to stipulate that it would not perform a “cutdown” procedure on Smith or give him an intramuscular sedative if his execution is carried out as scheduled. ADOC Commissioner John Hamm made that stipulation under oath in court today.

The state maintains that the stipulation effectively makes moot Smith’s claims that he could suffer if the state uses procedures outside its protocol.

Grass told the judge the Smith defense team should not have to take the ADOC’s word for what happened during the James’ execution because there were no independent witnesses. The portion of executions when the IV lines are established is not viewable by the media or witnesses.

“Frankly, your honor, the department hasn’t earned a great deal of trust in explaining what goes on,” Grass told the judge. Grass asked the judge to allow discovery, depositions, and cross examination in the case for an independent review of what happened in the James’ execution.

“We shouldn’t be required to take the word of the department on what happened,” Grass said.

The ADOC protocol for lethal injection protocol calls for two methods to establish a connection with a vein, either by standard access with a needle or by a central line procedure, which Assistant AG Anderson said would be typically done in the shoulder.

Huffaker asked Anderson how the ADOC determines when to move to the central line procedure and when to decide to call an execution off because of the difficulty tapping a vein, as it did with Miller in September and Hamm in 2018.

“Is it 10 pokes?” Huffaker asked “Is it 11? Is it 100? Is it one hour? What is it?”

Anderson said he did not know the answer.

Huffaker is the also judge in Miller’s lawsuit. Miller claimed that he chose execution by nitrogen hypoxia during a time when death row inmates had that option in 2018. The state maintains there is no record of that. Huffaker determined after a hearing it was substantially likely that Miller chose nitrogen hypoxia during the allowed time. The judge issued a preliminary injunction blocking the state from executing Miller other than by nitrogen hypoxia, a method that has never been used and is not ready. The state appealed to the U.S. Supreme Court, which in a 5-4 decision vacated Huffaker’s order, clearing the way for Miller’s execution to proceed.

That decision by the justices came at about 9 p.m. on Sept. 22, three hours after the execution was to begin. The state then tried to execute Miller but called it off because of the failure to tap a vein and concerns the procedure could not be finished by midnight.

The state is seeking a new execution date for Miller, who was convicted of killing three men in a Shelby County workplace shooting spree in August 5, 1999. Those men were Lee Holdbrooks, 32; Christopher Scott Yancy, 28; and Terry Jarvis, 39. Holdbrooks and Yancy were employees of Ferguson, while Jarvis worked for Post Airgas in Pelham.

Unlike Miller, Smith does not claim that he chose execution by nitrogen hypoxia. But his attorney Grass argued that Smith did not have the information to make an informed choice back in 2018 because there was no indication that the method nitrogen hypoxia method would still not be ready in October 2022.

The Legislature approved nitrogen hypoxia in 2018 as an alternative to lethal injection in response to legal challenges to lethal injection and difficulty in obtaining the drugs. The concept is that the condemned inmate would breathe only nitrogen and die from oxygen deprivation. But no state has ever carried out an execution that way and Alabama has not developed a protocol.

Today, Huffaker noted that he had received conflicting information from the state about its efforts to develop the nitrogen hypoxia method. During a hearing in Miller’s case, a lawyer for the state said it was “very likely” the state would have nitrogen hypoxia ready in time for Miller’s execution on Sept. 22.

“It’s been a moving target with me,” Huffaker said. “A year-plus ago I was told it would be ready in the spring of 2021.”

Assistant AG Anderson and ADOC Commissioner Hamm told the judge they did not know when nitrogen hypoxia would be ready.

“It is being developed but we do not have a protocol at this point,” Hamm said.

At the conclusion of today’s hearing, Huffaker told the lawyers he would issue a ruling on the state’s motion to dismiss Smith’s lawsuit but did not say when. Huffaker also went over a tentative schedule to proceed with the case. The judge told Grass to file his planned motion for a preliminary injunction by Oct. 19 and for the state to be ready to file a response by Oct. 26. He said Nov. 4 is a possible date for an evidentiary hearing in the case. The judge said he could then issue a ruling the following week, allowing the parties time to file an appeal before the scheduled execution date.

Read more: What is nitrogen hypoxia? Alabama’s new, untried execution method explained